Transition Metal-Catalyzed Alkyne Activation Comprising Cycloisomerization, Hydrative Carbocyclizaton and Oxidative Cleavage Reaction

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研究生：	達斯 Arindam Das
論文名稱：	Transition Metal-Catalyzed Alkyne Activation Comprising Cycloisomerization, Hydrative Carbocyclizaton and Oxidative Cleavage Reaction
指導教授：	劉瑞雄 Liu, Rai-Shung
口試委員:
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2009
畢業學年度：	97
語文別：	英文
論文頁數：	616
中文關鍵詞：	金催化、三鍵加成
外文關鍵詞：	Transition Metal-Catalyzed Alkyne Activation
相關次數：	點閱：2 下載：0
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中文摘要

本論文分為五個章節，主要是利用過渡金屬催化環化異構化、水合環化以及分子內氧化斷裂反應的研究。
第一章主要是探討過渡金屬催化分子內三鍵環內六環環化反應反應中伴隨著結構的重組並生成□的衍生物。我們發現反應是經由雙鍵的斷裂而造成亞烷基的轉移，而此類型的反應可很容易利用PtCl2、Zn(OTf)2，AuCl以及AuCl3催化進行反應。
第二章主要是探討利用三炔類化合物經由水合環化反應可得到雙螺環醇類化合物接著進行脫水反應可得到雙環酮類化合物。此反應是利用鉑催化經由選擇性的水合、三鍵的嵌入以及醛類化合物自身縮合反應。
第三章主要是探討一鍋化合成1，2-苯並菲的衍生物，反應利用PtCl2催化水合雙聚合反應生成二烷基一乙醯基苯。此反應經由三鍵選擇性的水合反應接著由雙酮基的中間體進行具有化學選擇性的雙聚化反應，而此類型的反應機構經由13C的標定實驗並分離出反應中間體進行驗證。
第四章主要是探討由氧化雙炔化合物利用過渡金屬PtCl2以及PPh3AuCl/AgOTf催化水合環化反應生成苯□喃酮以及三螺環酮。而在反應中發現三鍵上鄰近的取代基會進而影響產物的位像選擇性。
第五章主要是探討利用過渡金屬金在室溫下利用氧氣使芳香基炔醚類進行氧化斷裂，此類反應可應用再C-H，C-C以及C≡C的斷裂。

ABSTRACT

Transition metal-catalyzed cycloisomerization, hydrative carbocyclization and oxidative- cleavage of appropriately functionalized organic molecules are described in this dissertation. For sake of convenience and better understanding, the thesis is divided into five chapters.
In the first chapter a new metal-catalyzed 6-endo-dig cyclization of 1-(2-(2-methylprop-1-enyl)phenyl)prop-2-yn-1-ol has been described, which produces substituted naphthalene derivatives with structural reorganization. In this process, we observed a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization were manifested by its compatibility with a wide diverse substrates and π-alkyne activators including PtCl2, Zn(OTf)2, AuCl and AuCl3.
The second chapter deals with a novel hydrative cyclization of triynes to afford bicyclic spiro alcohols, which undergo subsequent dehydration to give bicyclic ketones. This platinum catalysis has proposed to comprise a sequence of cascade reactions including, two selective hydrations, alkyne insertion and aldol condensations.
The third chapter describes, one-pot syntheses of chrysene derivatives via PtCl2-catalyzed hydrative dimerization of readily available 2-alkynyl-1-acetylbenzenes. This new tandem catalysis comprises an initial selective hydration of the alkyne, followed by chemoselective dimerization of diketone intermediates. The mechanism of this cyclization has been elucidated by 13C-labeling experiments as well as isolation of reaction intermediates.
The fourth chapter presents a unique synthesis of benzopyrones and tricyclic spiroketones from hydrative carbocyclization of oxodiyne substrates catalyzed by PtCl2 and PPh3AuCl/AgOTf, respectively. These distinct carbocyclizations with Pt and Au catalysts stem from their altered regioselectivity in the oxo-assisted hydration of the neighboring alkyne carbons.
The last chapter discusses a gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen under ambient conditions; the transformation involves a remarkable cleavage of C-H, C-C and C≡C bonds simultaneous.

Contents

Acknowledgement                                    IV
Abstract                                                 VI
List of Schemes                                            VII
List of Tables                                            XIII
List of Publications                                        XVI
Abbreviations                                         XVIII

Chapter I: Metal-Catalyzed cycloisomerization of En-Yne Functionalities via 1,3-Alkylidene Migration
Introduction                                      1
Results and Discussion                                                                 14
Conclusion                                                                                    20
Experimental Procedure and Spectral Data                                  21
Reference                                                                                      35

Chapter II: PtCl2-Catalyzed Hydrative Cyclization of Trialkyne Functionalities to Form Bicyclic Spiro Ketones.
Introduction                                      38
Results and Discussion                                                                 48
Conclusion                                                                                    58
Experimental Procedure and Spectral Data                                  59
Reference                                                                                      74

Chapter III: Platinum-Catalyzed Chemoselectively Hydrative Dimerization of 2-Alkynyl-1-acetylbenzenes for One-Pot Facile Synthesis of Chrysene Derivatives.
Introduction                                      76
Results and Discussion                                                                 82
Conclusion                                                                                    94
Experimental Procedure and Spectral Data                                  95
Reference                                                                                      118

Chapter IV: Platinum- and Gold-Catalyzed Hydrative Carbocyclization of Oxo Diynes for One-Pot Synthesis of Benzopyrones and Bicyclic Spiro Ketones.
Introduction                                      121
Results and Discussion                                                                 132
Conclusion                                                                                    140
Experimental Procedure and Spectral Data                                  141
Reference                                                                                      163


Chapter V: Gold-Catalyzed Oxidative Cleavage of Aryl-Substituted Alkynyl Ethers using Molecular Oxygen. Simultaneous Degradation of C-H and Single and Triple Carbon-Carbon bonds under Ambient Conditions.
Introduction                                      165
Results and Discussion                                                                 176
Conclusion                                                                                    186
Experimental Procedure and Spectral Data                                  187
Reference                                                                                      204

  Crystal structures and 1H & 13 C NMR spectra                  207

List of Schemes

Chapter I
Scheme 1: Various pathways of enyne isomerization                2
Scheme 2: Skeletal reorganization vs. enyne metathesis                3
Scheme 3: Alder-ene cycloisomerization of enynes                                 4
Scheme 4: First example of cycloisomerization of enynes catalyzed by
platinum salt                                                                                                 4
Scheme 5: Pd(II) complex catalyzed skeletal reorganisation of
 1,6-enynes to 1-vinylcyclopentenes                                                            5
Scheme 6: Ru(II) catalyzed skeletal reorganisation of 1,6-
and 1,7-enynes                                                                                     6
Scheme 7: Carbocation analogy of Ru(II) catalyzed cycloisomerization          6
Scheme 8: Platinum-catalyzed skeletal rearrangment of enyne
 to a 1,3-diene                                                                                     7
Scheme 9: Synthesis of macrocyclic molecules via Platinum-
catalyzed  enyne cycloisomerization                                                      7
Scheme 10: Enyne cyclorearrangment in presence of aryl-and
 halide-substituted triple bonds                                                                       8
Scheme 11: Enyne cycloisomerization in presence of various gold catalyst     9
Scheme 12: Interpretation of metal-activated enynes in the sense of a
"Nonclassical" carbocation rendition                             10
Scheme 13: Ruthenium-catalyzd cycloisomerization of enynes
via 1,2-alkyl shift                                                                 10
Scheme 14: 1,3-alkylidene migration in the cycloisomerization
 of 1,6-enynes using AuPPh3+                                            11
Scheme 15: Orbital diagram of Fischer and Schrock carbene                  12
Scheme 16: Cyclopropanation of Pt-carbenes generated from
 5-en-1-yn-3-ol derivatives                                                                                13
Scheme 17: Intramolecular cyclopropanation of Au-carbenoids                      13
Scheme 18: General reaction                                                   14
Scheme 19: List of substrates                                                         14
Scheme 20: Synthesis of 1-(2-(2-methylprop-1-enyl)phenyl)prop-
2-yn-1-ol(1-1)                                                           13
Scheme 21: 13C labeling study to confirm 1,3-alkylidene migration               19
Scheme 22: Pt-catalyzed cycloisomerization of 1-(2-(2-methylprop-1-enyl)phenyl)but-2-yn-1-ol                                                                                  19
Scheme 23: Plausible Mechanism                                                                     20

Chapter II
Scheme 1: Qualitative orbital diagram showing the interaction between
                   a transition metal and an alkyne ligand.                                 39
Scheme 2: Hydrative carbocyclization of 1,6- and 1,7-diynes                   41
Scheme 3: Synthetic application of hydrative cyclization of 1,7-diynes    42
Scheme 4: Ru catalysed hydrative cyclization of tertiary1,6-diyneols        43
Scheme 5: Hydrative aromatisation of enediynes.                                 44
Scheme 6: Pd catalysed hydrative cyclisation of enediynes            44
Scheme 7: Gold-Catalyzed Hydrative Cyclization Reaction
of 1,6-Heptadiynes                                                                                     45
Scheme 8: Gold-catalyzed hydrative carbocyclisation of  1,5
 and 1,7- allenynes                                                                        46
Scheme 9: The active hydration catalyst in PtCl4 - CO catalyst system            47
Scheme 10: General reaction                                                    48
Scheme 11: Comperative hydration study of chemically
 two distinct alkyne                                                                    48
Scheme 12: List of substrates                                             49
Scheme 13: Synthesis of 1,2-bis(2-(prop-1-ynyl)phenyl)ethyne (2-1)        50
Scheme 14: Model reactions to simulate the cyclization mechanism        55
Scheme 15: Plausibility of a triketone intermediate                          56
Scheme 16: A proposed mechanism for the formation of spiro ketones          57
Scheme 17: Regio-selective hydration of alkyne via
 benzo[c]pyrylium intermediate                                                                            58

Chapter III
Scheme 1: The formation of chrysene by photochemical-oxidation
 of 1,6-diphenyl-1,3,5-hexatriene                                               78
Scheme 2: Reaction of benzyne with 1-vinylnaphthalene to form chrysene     78
Scheme 3: Synthesis of chrysene via acid-catalyzed rearrangement of cyclobutanones             79
Scheme 4: Synthesis of chrysene via titanium(IV)-catalyzed
 aldol-type condensation of silylenol ether with 2-arylacetaldehyde         79
Scheme 5: Synthesis of chrysene via twin annulation of naphthalene         80
Scheme 6: Synthesis of chrysene via intramolecular Diels-Alder reaction     80
Scheme 7: Benzopyrylium salt based synthesis of chrysene derivatives     81
Scheme 8: [TpRuPPh3(CH3CN)2]PF6-catalyzed cycization of
diyne-ene to chrysene                                                                                 81
Scheme 9: General reaction                                                          82
Scheme 10: List of substrates                                                          83
Scheme 11: Synthesis of 2-phenyl-1-(2-(prop-1-ynyl)phenyl)ethanone (3-1)     84
Scheme 12: Synthesis of 1-(2-(hex-1-ynyl)phenyl)ethanone (3-9)         85
Scheme 13: Synthesis of 1-(1-(prop-1-ynyl)naphthalen-2-yl)ethanone (3-19)     85
Scheme 14: Chemo- and regio-selectivity in platinum-catalyzed
 hydrative cyclization                                                                                 86
Scheme 15: Synthesis of polyaromatic compound                                  91
Scheme 16: 13C-labeling experiment                                                      93
Scheme 17: A Plausible Mechanism                                                      94

Chapter IV
Scheme 1: The neighboring group assisted metal-catalyzed
nucleophilic addition to alkyne                                                                            122
Scheme 2: Platinum catalyzed synthesis of 4-alkoxy-1-
naphthanal via benzopyrilium intermediate.                                    123
Scheme 3: Pt catalyzed synthesis of 8-oxabicyclo[3.2.1]octane
 frame work via benzopyrilium intermediate.                                                       124
Scheme 4: Gold-catalyzed annulation of oxoalkyne with Indole                  125
Scheme 5: Gold-catalyzed annulation of oxoalkyne with enol ether              125
Scheme 6: Intramolecular Huisgen-type reaction via platinum bound
pyrilium ion                                                                                                     126
Scheme 7: Metal-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)
benzenes with olefins via benzopyrilium intermediate                       127
Scheme 8: Synthesis of spiroketones via regio-selective alkyne hydration    128
Scheme 9: Platinum catalyzed regio-selective hydration and
dimerization to chrysene derivatives                                                            128
Scheme 10: Gold-catalyzed hydrative carbocyclization of
 2-(alk-2-yn-1-onyl)-1- alkynylbenzenes  and 1,5-diyn-3-ones               129
Scheme 11: Directed gold-catalyzed hydration of alkynes through
 neighboring group assistance                                                                130
Scheme 12: Benzopyrone framework in naturally occuring compounds     131
Scheme 13: General Reaction                                 131
Scheme 14: List of Substrates                                 132
Scheme 15: Synthesis of 1-(2-(2-(2-(prop-1-ynyl)phenyl)ethynyl)phenyl)ethanone(4-1)                         133
Scheme 16: Deuterium-labeling experiment                         137
Scheme 17: A plausible mechanism for formation of benzoisochromene         139
Scheme 18: A plausible mechanism for the formation of
bicyclic spiro ketone                                                                                           140

Chapter V
Scheme 1: Stoichiometric Reactions Involving Alkyne Cleavage         166
Scheme 2: Mortreux's discovery                                                      167
Scheme 3: Cross-metathesis                                                                167
Scheme 4: Ring closing alkyne metathesis                                                  168
Scheme 5: Rhodium-catalyzed cleavage of alkyne via hydroiminoacylation     169
Scheme 6: C-C triple bond cleavage of diynes through the
hydroamination with  transition metal catalysts                                        170
Scheme 7: Ru-catalyzed cleavage of C-C triple bonds of ethynyl alcohols      171
Scheme 8: Au-catalyzed cascade cyclization / oxidative cleavage
 of (Z)-enynols.                                                                                           172
Scheme 9: Lewis acid promoted palladium-catalyzed C-C triple
 bond cleavage with molecular oxygen                               172
Scheme 10: Five-Bond Cleavage in Copper-Catalyzed Skeletal
Rearrangement of O-Propargyl Arylaldoximes to b-Lactams            173
Scheme 11: Representative example of C=C double bond cleavage        174
Scheme 12: Metal-catalyzed C-C single bond cleavage of strained alkanes    175
Scheme 13: Cleavage of cyclohexane's C-C single bond with
Cobalt(II1) acetate                                                                                           176
Scheme 14: General Reaction                                 176
Scheme 15: List of Substrates                                 177
Scheme 16: Synthesis of 1-(1-methoxybut-2-ynyl)benzene (5-1)               177
Scheme 17: Mechanistic study                                                                      184
Scheme 18: A Plausible Mechanism                                               185

List of Tables
Chapter I
Table 1: The chemoselectivity in the cyclization of substrate (1-1) with various metal catalyst                                                                                                      16
Table 2: Zn(OTf)2-catalyzed cyclisation of various alcohols via
 1,3-alkylidene migration                                                                                   18

Chapter II
Table 1: Hydrative carbocyclization of compound (2-1) with various
 metal catalyst.                                                                                        51
Table 2: PtCl2-catalyzed hydrative cyclization of symmetric triynes              53
Table 3: Deuterium-Labeling Experiments                                 54

Chapter III
Table 1: Catalytic dimerization of 1-carbonyl-2-(prop-1-yn-1-yl)benzene
 over various acid catalysts.                                                                 88
Table 2: Catalytic Synthesis of Chrysenes from 2-Alkynyl-1-
acetylbenzenes                                                                             90
Table 3: Synthesis of benzothiophene based chrysene derivatives                  91
Chapter IV
Table 1: Classification of Ring-Closure Types                                123
Table 2: Chemoselectivity with Gold and Platinum Catalysts                  134
Table 3: Platinum-catalyzed synthesis of benzoisochromenes                  135
Table 4: Au(I)-Catalyzed synthesis of spiro ketones                                        136

Chapter V
Table 1: Screning of Metal-Catalyst for Oxidative Cleavage of Aryl
Substituted Alkynyl Ethers (5-1) using Molecular Oxygen            179
Table 2: Gold-catalyzed oxidative cleavage 4-phenyl-4-alkoxy-2-butyne       180
Table 3: Substrates scope of gold-catalyzed oxidative cleavage reaction         182
Table 4:                                                                                                        183

List of Figures

Chapter II

Figure 1: Alkyne-complex                                                                              39
Figure 2:                                                                                                          47
Figure 3: ORTEP drawing of bicyclic spiro ketone (2-11)                             52
Figure 4: Product distribution over reaction time                                           56

Chapter III

Figure 1: ORTEP drawing of compound (3-25)                                              87
Figure 2:  ORTEP drawing of compound (3-44)                                             92
Chapter IV

Figure 1: ORTEP drawing of bicyclic spiro ketone 4-32(A)                              137

                                

ChapterI
References :
(1) a) Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W.; Eds., Pergamon Press: Oxford, 1982; b) Green, M. L. H.; Davies, S.G. Philos. Trans. R. Soc. London A 1988, 326, 501; c) Collman, J.P.; Hegedus, L.S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, University Science Books: Mill Valley, California, 1987; d) Seebach, D. Angew. Chem. Int. Ed. Engl. 1990, 29, 1320.
(2) a) Trost, B. M. Acc. Chem. Res. 2002, 35, 695. b) Trost, B. M. Angew. Chem. 1995, 107, 285; Angew. Chem. Int. Ed. Engl. 1995, 34, 259. c) Trost, B. M. Science 1991, 254, 1471.
(3) a) Anastas, P.; Warner, J. C. in Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998. b) Anastas, P.T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686. c) Anastas, P. T.; Zimmerman, J. B. Environ. Sci. Technol. 2003, 37, 94A. d) Poliakoff, M.; Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science 2002, 297, 807. e) Trost, B. M.; Toste, D. F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
(4) See selected reviews: (a) Ma, S.-M.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200. (b) Bruneau, C. Angew. Chem. Int. Ed. 2005, 44, 2328. (c) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. (d) Mendez, M.; Mamane, V.; F□rstner, A. Chemtracts, 2003, 16, 397. (e) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
(5) a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635. c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
(6) a) Michelet, V.; Toullec, P. Y.; Genet, J.-P. Angew. Chem. Int. Ed. 2008, 47, 4268. b) F□rstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410. c) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. d) Zhang, L.; Sunm, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
(7) Mendez, M.; Munoz, M. P.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
(8) a) Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567. b) F□rstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863. c) Nevado, C.; Ferrer, C.; Echavarren, A. M. Org. Lett. 2004, 6, 3191.
(9) a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; b) Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 4753.
(10) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
(11) a) Trost, B. M.; Chang, V. K. Synthesis 1993, 824; b) F□rstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. c) F□rstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. Organometallics 1996, 15, 901. e) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. f) Bajracharya, G. B.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2005, 70, 892. g) Fernandez-Rivas, C.; Mendes, M.; Echavarren. J. Am. Chem. Soc. 2000, 122, 1221.
(12) a) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. b) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896. c) Jimenez-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333. d) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990. e) Hoffmann-Roder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387. f) Hashmi, A. S. K. Gold Bull. 2004, 37, 51. g) Arcadi, A.; Di Giuseppe, S. Curr. Org.Chem.2004, 8, 795. h) Bianchi, G.; Arcadi, A. Targets Heterocycl Syst. 2004, 8. 82. i) Dyker, G. Angew. Chem. Int. Ed. 2000, 39, 4237.
(13) a) Bond, G. C. Gold Bull. 1972, 5, 11. b) Haruta, M.; Kobayashi, T.; Sano, H.; Yamada, N. Chem. Lett. 1987, 405. c) Hutchings, G. J. J. Catal. 1985, 96, 292. d) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
(14) a) Nieto-Oberhuber, C.; Paz Munoz, M.; Bunuel, E.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 2402.
(15) Madhushaw, R.; Lo, C.-Y.; Hwang, C.-W.; Su, M.-D.; Shen, H.-C.; Pal, S.; Shaikh, I. R.; Liu, R.-S. J. Am. Chem. Soc. 2004, 126, 15560.
(16) Selected examples for metathesis-type products besides Grubbs’catalyst: (a) Trost, B. M.; Yanai, M.; Hoogstein, K. J. Am. Chem. Soc. 1993, 115, 5294. (b) Chatani, N. Kataoka, K.; Murai, S. Furukawa, N, Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104. (c) Mendez, M.; Munoz, M. P.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (d) F□rstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. (e) Nieto-Oberhuber, C.; Munoz, P. M.; Bunuel, E.; Nevado, C.; Cardenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 2402.
(17) (a) Zhang, L.; Sun, S.; Kozmin, S. Adv. Synth. Catal. 2006, 348, 2271. (b) Ma, S. M.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200. (c) Bruneau, C. Angew. Chem. Int. Ed. 2005, 44, 2328. (d) Hashmi, A. S. K.; Angew. Chem. Int. Ed. 2005, 44, 6990. (e) Echavarren, A. M., Nevado, C. Chem. Soc. Rev. 2004, 33, 431. c)Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouri□s, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
(18) Luzung, M. R.; Markham, J. P.; Toste, J. F. J. Am. Chem. Soc. 2004, 126, 10858.
(19) Tang, J. M.; Bhunia, S.; Sohel, S. M. A.; Lin, M. Y.; Liao, H. Y.; Datta, S.; Das, A.; Liu, R-.S. J. Am. Chem. Soc. 2007, 129, 15677.
(20) For the 5-exo-dig cyclizations of 1,6-enynes, see references: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553. (b) Nevado, C.; C□rdenas, . J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627. (c) Amijs, C. H. M.; Ferrer, C.; Echavarren, A. M. Chem. Commun. 2007, 698. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genet, J.-P. Chem. Commun. 2004, 850.
(21) Chan, W.-C.; Lau, C.-P.; Chen, Y.-Z.; Fang, Y.-Q.; Ng, S.-M.; Jia, G. Organometallics 1997, 16, 34.
Chapter II
References :
1)a) Tietze, L. F.; Beifuss, U. Sequential transformations in organic chemistry: a synthesis strategy with a future. Angew. Chem. Int. Ed. Engl. 1993, 32, 131. b) Tietze, L. F. Domino Reactions in Organic Synthesis. Chem. Rev. 1996, 96, 115.
2)A) Dewar, M. J. S. Bull. Soc. Chim. Fr. 1951, 18, C71-C79. b) Chatt, J.; Duncanson, L. A. J. Chem. Soc. 1953, 2939-2947.
3)D. M. P. Mingos in Comprehensive Organometallic Chemistry, Vol. 3 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, pp. 1-88. b) Frenking, G.; Frohlich, N. Chem. Rev. 2000, 100, 717. c) Dedieu, A. Chem. Rev. 2000, 100, 543, and references therein.
4)Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
5)Trost, B. M. Science 1991, 254, 1471-1477.
6)Kucherov, M. Chem. Ber. 1881, 14, 1540-1542.
7)For an excellent review on alkyne hydration, see: Hintermann, L.; Labonne, A. Synthesis 2007, 1121-1150.
8)a) Schrohe, A. Chem. Ber. 1875, 8, 367; b) Baeyer, A. Ber. 1882, 15, 2705; c) Perkin, W. H., Jr. J. Chem. Soc. 1884, 45, 170; d) Tsuchimoto, T.; Joya, T.; Shirakawa, E.; Kawakami, Y. Synlett 2000, 12, 1777; e) Izumi, Y. Catal. Today 1997, 33, 371; f) Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171.
9)a) Drenth, W.; Hogeveen, H.; Recl. Trav. Chim. Pays-Bas 1960, 79, 1002.; b) Allen, A. D.; Chiang, Y.; Kresge, A. J.; Tidwell, T. T. J. Org. Chem. 1982, 47, 775, and references their in.
10)Thomas, R. J.; Campbell, K. N.; Hennion, G. F. J. Am. Chem. Soc. 1938, 60, 718.; b) Stacy, G. W.; Mikulec, R. A. in Organic Syntheses, Coll. Vol. 4 (Ed.: N.Rabjohn), Wiley, New York, 1963, 13.; c) Olah, G. A.; Meider, D. Synthesis 1978, 671.
11)a) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2003, 125, 11516. b) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599. c) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2005, 127, 4763. d)Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467. e) Odedra, A.; Wu, C.-J.; Pratap, T. B.; Huang, C.-W.; Ran, Y.-F.; Liu, R.-S. J. Am. Chem. Soc. 2005, 127, 3406.
12)Lee, C.- Y.; Wu, M. -J. Eur. J. Org. Chem. 2007, 21, 3463.
13)a) Zhang, C.; Cui, D-. M.; Yao, L-. Y.; Wang, B-. S.; Hu, Y-. Z.; hayashi, T. J. Org. Chem. 2008, 73, 7811. b) Yang, C.-Y.; Lin, G.-Y.; Liao, H.-Y.; Datta, S.; Liu, R.-S. J. Org. Chem, 2008, 73, 4907.
14) Baidossi, W.; Lahav, M.; Blum, M. J. Org. Chem. 1997, 62, 669.
15)(a) Bayer, O. In Houben-Weyl: Methoden der Organische Chemie; Muller, E., Ed.; G. Thieme Verlag: Stuttgart, 1954; Vol. VII, Part 1. (b) Juger, V.; Viehe, H. G. In Houben-Weyl: Methoden der Organische Chemie; Muller, E., Ed.; G. Thieme Verlag: Stuttgart, 1977; Vol. V/2a. c) Harman, W. D.; Dobson, J. C.; Taube, H. J. Am. Chem. Soc. 1989, 111, 3061. d) Blum, J.; Huminer, H.; Alper, H. J. Mol. Catal 1992, 75, 153.
16)a) Jimenez-Nunnez, E.; Echavarren, A. M. Chem. Commun. 2007, 333. b) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990. c) Muzart, J. Tetrahedron, 2008, 64, 5815.
17)Only highly enolizable ketones can be cyclized onto alkynes[17a] and alkenes[17b] by using suitable catalysts, see, for example: a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526. b) Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056.
18)This system is proposed to form PtCl2(CO)n; see: a) F□rstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244; b) F□rstner, A.; A□ssa, C. J. Am. Chem. Soc. 2006, 128, 6306; c) F□rstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024.
19)Selected examples for metal-catalyzed hydration of alkynes, see: a) Hiscox, W.; P. W. Jennings, P. W. Organometallics, 1990, 9, 1997; b) Baidossi, W.; Lahav, M.; Blum, J. J. Org. Chem. 1997, 62, 669; c) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729; d) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem. 2002, 114, 4745-4747; Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
20)For this 6-endo-dig cyclization, see: a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; b) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458.

Chapter III
References :
(1) (a) Kishi, Y. Pure Appl. Chem. 1993, 65, 771. (b) Suh, E. M.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 11205.
(2) (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew.Chem., Int. Ed. Engl. 1993, 32, 131. (b) See also: Tietze, L. F. Chem. Ind. 1995, 453. (c) Waldmann, H. “Domino Reaction” in Organic Synthesis Highlight II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 193-202. (d) Hall, N. Science 1994, 266, 32.
(3) For general reviews, see: (a) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York, 1994; p 79. (b) Tietze, L. F. Chem. Rev. 1996, 96,115. (c) Winkler, J. D. Chem. Rev. 1996, 96,167. (d) Denmark, S.E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
(4) For selected examples, see: (a) de Meijere, A.; von Zezschwitz, P.; Brase, S. Acc. Chem. Res. 2005, 38, 413. (b) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 7786. (c) Patel, S. J.; Jamison, T. F. Angew. Chem. Int. Ed. 2003, 42, 1364. (d) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew. Chem. Int. Ed. 2004, 43, 3935. (e) Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem. Int. Ed. 1992, 31, 645. (f) Yoshida, M.; Fujita, M.; Ishii, T.; Ihara, M. J. Am. Chem. Soc. 2003, 125, 4874. (g) Varela, J. A.; Rubin, S. G.; Gonzalez-Rodriguez, C.; Castedo, L.; Saa, C. J. Am. Chem. Soc. 2006, 128, 9262.
(5) For selected reviews, see: (a) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813. (b) Grigg, R. J. Heterocycl. Chem. 1994, 31. 631. (c) de Meijere, A.; Meyer, P. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (d) Nie, Y.; Niah, W.; Jaenicke, S.; Chuah, G. K. J. Catal. 2007, 248, 1. (e) Ray, D.; Ray, J. K. Org. Lett. 2007, 9, 191. (f) Quinn, K. J.; Isaacs, A. K.; Arvary, R. A. Org. Lett. 2004, 6, 4143.
(6) For selected examples, see: (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (b) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042. (c) Trost, B. M.; Shen, H. Angew. Chem., Int. Ed. 2001, 40, 2313. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. 1997, 36, 2632. (e) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002, 124, 6512.
(7) Masakazu, F. Eur. Pat. EP 1 561 794 A1.
(8) (a) Eckert, J.-F.; Nicoud, J.-F.; Nierengarten, J.-F.; Liu, S.-G.; Echegoyen, L.; Armaroli, N.; Barigelletti, F.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. J. Am. Chem. Soc. 2000, 122, 7467. (b) Cravino, A.; Sariciftci, N. S. J. Mater. Chem. 2002, 12, 1931. (c) El-Ghayoury, A.; Schenning, A. P. H. J.; van Hal, P. A.; van Duren, J. K. J.; Janssen, R. A. J.; Meijer, E. W. Angew. Chem., Int. Ed. 2001, 40, 3660. (d) Pourtois, G.; Beljonne, D.; Cornil, J.; Ratner, M. A.; Bredas, J. L. J. Am. Chem. Soc. 2002, 124, 4436.
(9) (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99. (b) Horowitz, G. Adv. Mater. 1998, 04, 365. (c) Cai, X.; Hara, M.; Kawai, K.; Tojo, S.; Majima, T. Chem. Phys. Lett. 2003, 368, 365.
(10) a) Atkinson, G. H.; Gilmore, D. A.; Dosser, L. R.; Pallix, J. B. J. Phys. Chem. 1982, 86, 2305. b) Beck, S. M.; Brus, L. E.; J. Chem. Phys. 1981, 75, 1031. c) Atkinson, G. H.; Dosser, L. R.; J. Chem. Phys. 1980, 72, 2195. d) Koshihara, S.; Kobayashi, T. J. Chem. Phys. 1986, 85, 1211.
(11) Johnston, L. J.; Redmond, R. W. J. Phys. Chem. A 1997,101, 4660.
(12) McGimpsey, W.G.; Samaniego, W. N.; Chen, L.; Wang, F. J. Phys. Chem. 1998, 102, 8679.
(13) For chrysene synthesis, see references 14 and (a) Clar, E. Polycyclic Hydrocarbons, Academic Press: New York 1964. (b) Wood, C. S.; Mallory, F. B. J. Org. Chem. 1964, 29, 3373. (c) Lee-Ruff, E.; Hopkinson, A. C.; Dao, L. H. Can. J. Chem. 1981, 59, 1675. (d) Gore, P. H.; Kamonah, F. S. Synthesis 1978, 773. (e) Davies, W; Wilmshurst, J. R. J. Chem. Soc. 1961, 4079. (f) Corbett, T. G.; Porter, Q. N. Aust. J. Chem. 1965, 18, 1781. (g) Levy, L. A.; Sashikumar, V. P. J. Org. Chem. 1985, 50, 1760. h) Fonken, G. J Chem. Ind. 1962, 1327.
(14) For chrysene synthesis using functionalized naphthalenes: (a) Fonken, G. F. Chem. Ind. (London) 1962, 1327. (b) LeHoullier, C. S.; Gribble, G. W. J. Org. Chem. 1983, 48, 1682. (c) Blackburn, E. V.; Loader, C. E.; Timmons, C. J. J. Chem. Soc. 1970, 163. (d) Leznof, C. C.; Hayward, R. J. Can. J. Chem. 1972, 50, 528. (e) Leznof, C. C.; Hayward, R. J. Can. J. Chem. 1970, 48, 1842. (f) Carruthers, W.; Evans, N.; Pooranamoorthy, R. J. Chem. Soc. 1973, 144. (g) Casagrande, M.; Gennari, G.; Cauzzo, G. Gazz. Chim. Ital. 1974, 104, 1251. (h) Masetti, F.; Bartocci, G.; Galiazzo, G. Gazz. Chim. Ital. 1975, 105, 419. (i) Nagel, D. L.; Kupper, R.; Antonson, K.; Wallcave, L. J. Org. Chem. 1977, 42, 3626. (j) Harvey, R. G.. Tetrahedron Lett. 1988, 29, 3885. (k) Lyle, T. A.; Daub, G. H. J. Org. Chem. 1979, 44, 4933.
(15) (a) Korobka, Kuznetsov, E. V. Khim. Geterotsikl. Soedin. 1982, 1184. (b) Korobka, I. V.; Voloshina, A. I.; Kuznetsov, E. V. Khim. Geterotsikl. Soedin. 1984, 1472. (c) Korobka, I. V.; Revinskii, Yu. V.; Kuznetsov, E. V. Khim. Geterotsikl. Soedin. 1985, 910.
(16) For synthesis of benzopyrylium salt, see the review paper: Kuznetsov, E. V.; Shcherbakova, I. V.; Balaban, A. T. Adv. Heterocycl. Chem. 1990, 50, 157-254.
(17) Shen, H. –C.; Tang, J.-M.; Chang, H.-K.; Yang, C.-W.; Liu, R.-S. J. Org. Chem. 2005, 70, 10113.
(18) Chang, H.-K.; Datta, S.; Das, A.; Odedra, A.; Liu, R.-S. Angew. Chem. Int. Ed. 2007, 46, 4744.
(19) In the presence of CO, PtCl2 was thought to form PtCl2(CO)n which showed better electrophilicity for alkyne; see (a) F□rstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244. (b) F□rstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024. (c) F□rstner, A.; C, Aissa. J. Am. Chem. Soc. 2006, 128, 6306. (d) Taduri, B. P.; Ran, Y.-F.; Huang, C.-W.; Liu, R. -S. Org. Lett. 2006, 8, 883. (e) Lo, C.-Y.; Lin, C.-C.; Cheng, H.-M.; Liu, R.-S. Org. Lett. 2006, 8, 3153.
(20) (a) Stille, J. K. Angew. Chem. Int. Ed. 1986, 25, 508. (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636. (c) Sonogashira, K.; In Handbook of Organopalladium Chemistry for Organic synthesis; Negishi, E.-i.; Ed; Wiley-Interscience: New York, 2002, pp 493-529. (d) Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979. (e) Tykwinski, R. R. Angew. Chem. Int. Ed. 2003, 42, 1566.
(21) Selected examples: (a) Zhao, C.; Zhang, Y.; Ng, M.-T. J. Org. Chem. 2007, 72, 8384. (b) Silva, N. O.; Abreu, A. S.; Ferreira, P. M. T.; Monteiro, L. S.; Queiroz, M.-J. R. P. Eur. J. Org. Chem. 2002, 2524. (c) Wang, Z.; Elokdah, H.; McFarlane, G.; Pan, S.; Antane, M. Tetrahedron Lett. 2006, 47, 3365.
(22) (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (b) Iwasawa, N.; Shido, M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814.
(23) (a) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921. (b) Asao, N.; Aikawa, H. J. Org. Chem. 2006, 71, 5249.
Chapter IV
References :
(1) Horva´th, I. T.; Anastas, P. T. Chem. Rev. 2007, 107, 2169.
(2) (a) Trost, B. Acc. Chem. Res. 2002, 35, 695. (b) Trost, B. Science 1991, 254, 1471. (c) Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505.
(3) Kummerer, K. Green Chem. 2007, 9, 899. (b) Hofer, R.; Bigorra, J. Green Chem. 2007, 9, 203.
(4) Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
(5) Anastas, P. T.; Kirchhoff, M. M.; Williamson, T. C. Appl. Catal. A: Gen. 2001, 221, 3.
(6) Liu, S.; Xiao, J. J. Mol. Catal. A: Chem. 2007, 270, 1.
(7) (a) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127.; (b) Detert, H.; Meier, H. Liebigs Ann./Recl. 1997, 1565.; (c) Utimoto, K. Pure Appl. Chem. 1983, 55, 1845.; (d) Stork, G.; Borch, R. J. Am. Chem. Soc. 1964, 86, 935.; (e) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237–4245.; (f) Arcadi, A.; Cerichelli, G.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Tetrahedron Lett. 2000, 41, 9195–9198.; (g) Jennings, P. W.; Hartman, J. W.; Hiscox, W. C. Inorg. Chim. Acta 1994, 222, 317–322.
(8) a) Baldwin, J. E. "Rules for Ring Closure." J. C. S. Chem. Comm.. 1976, 18, 734-736.; b) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A: Structures and Mechanisms, 3rd ed.; Plenum Press: New York, 1990; pp. 165-167.; c) Baldwin, J. E. "Rules for Ring Closure: Ring Formation by Conjugate Addition of Oxygen Nucleophiles." J. Org. Chem. 1977,42, 3846.
(9) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605.
(10) Kusama, H.; Ishida, K.; Funami, H.; Iwasawa, N. Angew. Chem. Int. Ed. 2008, 47, 4903.
(11) Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814.
(12) Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944.
(13 a) Kim, N.; Kim, Y.; Park, W.; Sung, D.; Gupta, A. K.; Oh, C. H. Org. Lett. 2005, 7, 5289; b) Oh, C. H.; Ryu, J. H.; Lee, H. I. Synlett 2007, 2337. c) Oh, C. H.; Lee, J. H.; Lee, S. J.; Kim, J. I.; Hong, C. S. Angew. Chem. Int. Ed. 2008, 47, 7507.
(14) Asao, N.; Kasahara, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2003, 42, 3504.
(15) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458.
(16) Dyker, G.; Hildebrandt, D.; Liu, J.; Merz, K. Angew. Chem. Int. Ed. 2003, 42, 4399.
(17) For a review about hydration of alkynes see: Hintermann, L.; Labonne, A. Synthesis 2007, 112, 1–1150.
(18) Chang, H.-K.; Datta, S.; Das, A.; Odedra, A.; Liu, R.-S. Angew. Chem. Int. Ed. 2007, 46, 4744
(19) Das, A.; Liao, H. -H.; Liu, R.-S. J. Org. Chem. 2007, 72, 9214.
(20) Tang, J.-M.; Liu, T.-A.; Liu, R.-S. J. Org. Chem, 2008, 73, 8479.
(21) Wang, w.; Xu, B.; Hammnod, G. B. J. Org. Chem, 2009, 74, 1640.
(22) (a) Horii, S.; Fukase, H.; Mizuta, E.; Hatano, K.; Mizuno, K. Chem. Pharm. Bull. 1980, 28, 3601. (b) Nakano, H.; Matsuda, Y.; Ito, K.; Ohkubo, S.; Morimoto, M.; Tomita, F. J. Antibiot. 1981, 34, 266. (c) Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568. (d) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (e) Futagami, S.; Ohashi, Y.; Imura, K.; Ohmori, K.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 2000, 41, 1063. (f) Ishii, H.; Ishikawa, T.; Haginiwa, J. Yakugaku Zasshi 1977, 97, 890. (g) Ishii, H.; Ishikawa, T.; Murota, M.; Aoki, Y.; Harayama, T. J. Chem. Soc., Perkin Trans. I 1993, 1019.
(23) (a) F□rstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244. (b) F□rstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024. (c) Zhang, G,; Catalano, V. J,; Zhang, L. J. Am. Chem. Soc. 2007, 129, 11358. (d) Taduri, B. P.; Ran, Y.-F.; Huang, C.-W.; Liu, R. -S. Org. Lett. 2006, 8, 883. (e) Lo, C.-Y.; Lin, C.-C.; Cheng, H.-M.; Liu, R.-S. Org. Lett. 2006, 8, 3153.
(24) For platinum-catalyzed water-gas shift reaction, see: Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941.
(25) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
(26) For divergent reactivities between platinum and gold catalysts, see: (a) Zhang, G.; Catalano V.; Zhang L. J. Am. Chem. Soc. 2007, 129, 11358. (b) Hashimi, A. S. K.; Kurpejovic, E.; Frey, W.; Bats, J. W. Tetrahedron 2007, 63, 5879. (c) Godet, T.; Vaxelaire, C.; Michel, C.; Milet, A.; Belmont, P. Chem. Eur. J. 2007, 13, 5632.
Chapter V
References :
(1) (a) M. Murakami and Y. Ito, in Topics in Organometallic Chemistry, ed. S. Murai, Springer, Berlin, Germany, 1999, pp. 97–129 and references therein.
(2) C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610.
(3) For reviews, see: (a) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (b) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (c) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
(4) (a) Moriarty, R. M.; Penmasta, R.; Awasthi, A. K.; Prakash, I. J. Org. Chem. 1988, 53, 6124. (b) Sawaki, Y.; Inoue, H.; Ogata, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1133. (c) Chamberlin, R. L. M.; Rosenfeld, D. C.; Wolczanski, P. T.; Lobkovsky, E. B. Organometallics 2002, 21, 2724. (d) Figueroa, J. S.; Cummins, C. C. J. Am. Chem. Soc. 2003, 125, 4020. (e) O’Connor, J. M.; Pu, L. J. Am. Chem. Soc. 1990, 112, 9013. (f) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585. (g) Cairns, G. A.; Carr, N.; Green, M.; Mahan, M. F. Chem. Commun.1996, 2431. (h) Hayashi, N.; Ho, D. M.; Pascal, R. A., Jr. Tetrahedron Lett. 2000, 41, 4261.
(5) (a) Pennella, F.; Banks, R. L.; Bailey, G. C. Chem. Commun., 1968, 1548. (b) A. Mortreux and M. Blanchard, J. Chem. Soc., Chem. Commun., 1974, 786; (c) A. Mortreux, N. Dy and M. Blanchard, J. Mol. Catal., 1975, 1, 101; (c) A. Mortreux, F. Petit and M. Blanchard, Tetrahedron Lett., 1978, 4967; (d) A. Bencheick, M. Petit, A. Mortreux and F. Petit, J. Mol. Catal., 1982, 15, 93; (e) A. Mortreux, J. C. Delgrange, M. Blanchard and B. Lubochinsky, J. Mol. Catal., 1977, 2, 73; (f) A. Mortreux, F. Petit and M. Blanchard, J. Mol. Catal., 1980, 8, 97. (g) N. Kaneta, T. Hirai, M. Mori, Chem. Lett. 1995, 627. (h) F□rstner, A.; Seidel, G. Angew.Chem. Int. Ed. 1998, 37, 1734. (i) F□rstner, A.; Davies, P. W. Chem. Cmmun., 2005, 2307.
(6) (a) Jun, C.-H. Chem. Soc. Rev., 2004, 33, 610. (b) Jun, C.-H.; Lee, H.; Hong, J.-B.; B.-I. Kwon, Angew. Chem., Int. Ed. 2002, 41, 2146. (c) Lee, D.-Y.; Hong, B.-S.; Cho, E.-G.; Lee, H.; Jun, C.-H. J. Am. Chem. Soc. 2003, 125, 6372. (d) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc, 2003, 125, 6646.
(7) (a) Datta, S.; Chang, C.-L.; Yeh, K.-L.; Liu, R.-S. J. Am. Chem. Soc, 2003, 125, 9294. (b) Shen, H.-C.; Su, H.-L.; Hsueh Y.-C.; Liu, R.-S. Organometallics, 2004, 23, 4332. (c) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
(8) Liu, Y., Song, F.; Guo, S. J. Am. Chem. Soc. 2006, 128, 11332.
(9) Wang, A.; Jiang, H. J. Am. Chem. Soc. 2008, 130, 5030.
(10) ) Nakamura, I.; Araki, T. Terada, M. J. Am. Chem. Soc. 2009, 131, 2804.
(11) Lee, D. G.; Chen, T. Cleavage Reactions. In Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 541-591.
(12) Shing, T. K. M. In ComprehensiVe Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 703- 716.
(13) (a) Bailey, P. S. Chem. Rev. 1958, 58, 925-1010. (b) Criegee, R. Angew. Chem. Int. Ed. Engl. 1975, 14, 745-752. (c) Larock, R. C. In ComprehensiVe Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 1213-1215.
(14) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
(15) (a) Berkowitz, L. M.; Rylander, P. N. J. Am. Chem. Soc. 1958, 80, 6682. (b) Shalon, Y.; Elliott, W. H. Synth. Commun. 1973, 3, 287. (c) Lee, D. G.; Chen, T.; Wang, Z. J. Org. Chem. 1993, 58, 2918. (d) Wiberg, K. B.; Saegebarth, K. A. J. Am. Chem. Soc. 1957, 79, 2822. (e) Freeman, F.; Yamachika, N. J. J. Am. Chem. Soc. 1970, 92, 3730.
(16) (a) Drago, R. S.; Corden, B. B.; Barnes, C. W. J. Am. Chem. Soc. 1986, 108, 2453. (b) Neumann, R.; Abu-Gnim, C. J. Chem. Soc., Chem. Commun. 1989, 1324. (c) Neumann, R.; Abu-Gnim, C. J. Am. Chem. Soc. 1990, 112, 6025. (d) Steckhan, E.; Kandzia, C. Synlett 1992, 139-140.
(17) Crabtree, R. H. Chem. Rev. 1985, 85, 245-269.
(18) (a) Hogeveen, H.; Volger, H. C. J. Am. Chem. Soc., 1967, 89, 2486. (b) Gassman, P. G.; Atkins, T. J.; Lumb, J. T. J. Am. Chem. Soc. 1972, 94, 7757. (c) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc., 1970, 92, 3515.
(19) (a) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc., 1994, 116, 10 779; (b) Jun, C.-H.; Kang, J.-B.; Lim, Y.-G. Tetrahedron Lett., 1995, 36, 277; (c) McNeill, K. R.; Andersen, A.; Bergman, R. G. J. Am. Chem. Soc., 1997, 119, 11 244. (d) Onopchenko, A.; Schulz, J. G. D. J. Org. Chem.,1978, 38, 3729.
(20) For formation mechanism of enone 5-19, see selected examples: (a) Engel,D. A.; Dudly, G. B. Org. Lett. 2006, 8, 4027. (b) Edens, M.; Doerner, D.; Chase, C. R.; Nass, D.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 1977. (c) Andres, J.; Cardenas, R.; Silla, E.; Tapia, O. J. Am. Chem. Soc. 1988, 110, 666. (d) Meyer, K. H.; Schuster, K. Chem. Ber. 1922, 55, 819.
(21) (a) Liu, Y.-H.; Song, F.-J.; Guo, S.-H. J. Am. Chem. Soc. 2006, 128, 11332; (e) Wang, W.; Jiang, H. J. Am. Chem. Soc. 2008, 130, 5030.
(22) For electrophilic activation of vinylgold(I) complex, see: (a) Shi, Y.; Ramgren, S. D.; Blum, S. A. Organometallics, 2009, 28, 1275; (b) Hashmi, A. S. K.; Ramamurthi, T. D.; Rominger, F. J.Organomet.Chem. 2009, 694, 592; (c) Liu, L-P.; Xu, B.; Mashuta, M. S.; Hammond, G. B. J. Am. Chem. Soc. 2008, 130, 17642. (d) Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. Angew. Chem. Int. Ed. 2009, 48, 3112.
(23) Gibson, D. H.; Owens, K.; Ong, T.-S. J. Am. Chem. Soc. 1984, 106, 1125.

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