鈀金屬錯合物催化親核試劑與親電子試劑至不飽和碳-碳鍵上之加成反應

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研究生：	捷格默罕 Masilamani Jeganmohan
論文名稱：	鈀金屬錯合物催化親核試劑與親電子試劑至不飽和碳-碳鍵上之加成反應 Palladium-Catalyzed Addition Reactions of Electrophiles and Nucleophiles into Carbon-Carbon Multiple Bonds
指導教授：	鄭建鴻 Chien-Hong Cheng
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：	2005
畢業學年度：	93
語文別：	英文
論文頁數：	197
中文關鍵詞：	鈀金屬錯合物、催化、親核試劑、親電子試劑、加成反應
外文關鍵詞：	Palladium, Catalyzed, Nucleophiles, Electrophiles, Addition Reactions
相關次數：	點閱：102 下載：0
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在此本論文中是利用鈀金屬錯何物催化親核性試劑與親電子試劑至不飽和碳-碳鍵上之加成反應。而此論文主要分為四個章節，在第一章中主要是提到利用鈀金屬錯何物催化具活性的烯類、丙烯基氯化物及丙二烯基錫金屬化合物進行三分子偶合反應，而得到及高產率的1,7-烯炔化合物。而此反應亦可擴大至雙烯的反應中，並推測可能之進行的反應機制。第二章中主要是提到利用鈀金屬錯何物催化具活性的苯炔化合物、丙烯基氯化物及炔基錫金屬化合物進行三分子偶合反應，而得到及高產率的1,6-烯炔化合物。而此反應亦可擴大至雙烯及烯基錫金屬化合物，並推測其可能之反應機制。第三章中是利用鈀金屬錯何物催化雙烯、錫-鍺金屬化合物及烷基碘化物進行反應，而得到極高產率的產物。而此反應亦可擴大至分子內進行相同的反應而得到產物，並於最後推測其可能之反應機制。第四章中是利用鈀金屬錯何物催化雙烯、錫-矽化合物進行反應，而得到及高產率之產物，而配位基在此反應中扮演相當重要的角色，並推測可能進行之反應機制。

The thesis delineates the palladium catalyzed addition reactions of electrophiles and nucleophiles into carbon-carbon multiple bonds. This thesis is divided into four chapters. First chapter explains the synthesis of 1,7-enyne derivatives, the second chapter describes synthesis of 1,6-enynes, 1,6-enallenes and 1,6-dienes, the third chapter deals with the synthesis of substituted 2-arylallylgermanes, cyclicallylgermanes and cyclicallylsilanes and chapter 4 explains (E)-vinylicsilanes having allylstannanes in brief way.
Chapter 1 describes palladium catalyzed propargylallylation reactions of activated olefins. The three component addition reaction of allylic chlorides and allenylstannaes with activated olefins in the presence of palladium catalyst affords 1,7-enyne derivatives with high regio-, stereo and chemoselectivity in good to excellent yields. The reaction proceeds with various substituted activated olefins. Furthermore, the reaction was successfully extended to an activated dienes. A plausible mechanism based on □1-allenyl □3-allyl palladium intermediate is proposed to account for the catalytic three-component reaction.
Chapter 2 demonstrates the addition reactions of allylalkynyl, allylallenyl and allylalkenyl to benzynes in the presence of palladium catalyst. The reactions of allylic chlorides and alkynylstannanes into benzynes in the presence of palladium catalyst gave various 1-allyl-2-alkynylbenzenes in excellent yield. The reaction proceeds with various substituted benzyne precursors, allylic chlorides and alkynyl, allenyl and alkenylstannanes. This method allows an efficient synthesis of various 1-allyl-2-alkynylbenzenes, 1-allyl-2-allenylbenzenes and 1-allyl-2-alkenylbenzenes in good to excellent yields. Furthermore, the utility of 1-allyl-2-alkynylbenzenes in organic synthesis were successfully demonstrated with the synthesis of multiple rings. A possible mechanism for the present catalytic reaction is proposed.
Chapter 3 describes the synthesis of substituted 2-arylallylgermanes in a highly regio-, stereo- and chemoselective fashion involving a three-component assembly of allenes, aryl iodides and stannylgermane catalyzed by phosphine-free palladium complexes. The present catalytic reaction is highly regioselective in which aryl group and metal add to the middle and unsubstituted terminal carbon of the allene moiety, respectively. In addition, the reaction is highly stereoselective to give Z-isomer as an exclusive product. Furthermore, the catalytic reaction was successfully extended into partially intermolecular version to give cyclic metal reagents with excellent yields. The high chemoselectivity of the present reaction is due to a favorable SE2 cyclic pathway involved in transemetalation step. The mechanism involving a face-selective coordination of allenes is proposed to account for the high stereoselectivity.
Chapter 4 explains a highly regio- and stereoselective silylstannation of allenes using phosphine free palladium complexes. The addition reaction of trimethy(tributylstannyl)silane with allenes in the presence of phosphine-free palladium catalyst provided (E)-vinylicsilane having allylstannane moieties in excellent yield. The vinylic silanes and allyl stannanes present in these products allow for a large variety of chemical modifications. The nature of the ligand on the palladium complexes has a tremendous influence on the regio- and stereochemistry of present reactions.

TABLE OF CONTENTS

    Page
CHAPTER 1: Highly Regio- and Chemoselective
Palladium-Catalyzed Propargylallylation of Activated Olefins:
A Novel Route to 1-7-Enynes Derivatives
      Introduction    1
      Results and Discussion    7
      Conclusion    35
      Experimental Section    36
      References    57
CHAPTER 2: Palladium-Catalyzed Allylalkynylation, Allyl-
allenylation, and Allylalkenylation of Benzynes: a Highly Efficient
Route to 1,2-Disubstituted Arenes

      Introduction    63
      Results and Discussion    72
      Conclusion    95
      Experimental Section    95
      References    118
CHAPTER 3: Highly Regio-,Stereo-, and Chemoselective Aryl-
germation and Arylsilation of Allenes Catalyzed by Phosphine-free
Palladium Complexes: An Efficient Route to a new classes of
2-arylallylmetal reagents

      Introduction    121
      Results and Discussion    134
      Conclusion    153
      Experimental Section    154
      References    172
CHAPTER 4: Highly Regio- and Stereoselective Silylstannantion of
allenes Catalyzed by Phosphine-free Palladium Complexes
      Introduction    176
      Results and Discussion    180
      Conclusion    189
      Experimental Section    190
      References    196

List of Schemes

Chapter 1
        Page
1.1    Palladium-Catalyzed addition reactions of Allylic
Chlorides 5a-e, Allenylstannanes 12a and Aryl-
ethylidene Malononitrile 6a-g     7
1.2    Synthesis of Arylethylidene Malononitrile 6a-e     9
1.3    Synthesis of Heterocyclicethylidene Malononitrile 6f-g     10
1.4    Synthesis of n-Tributylallenylstannane 12a     11
1.5    Effects of the Leaving group on the Allylic Substrate of the Propargylallylation Reaction     12
1.6    Palladium-Catalyzed addition reactions of Allylic Chlorides 5a-e and Allenylstannane 12a into (Arylmethylene)-1,3-indanediones 19a-j    18
1.7    Synthesis of Substituted (Arylmethylene)-1,3-indanediones 19a-j     19
1.8    Palladium-Catalyzed Propargylallylation 2-2-Dimethyl-
5-(arylmethylene)-1,3-dioxane-4,6-diones 8a-b     24
1.9    Synthesis of Substituted 2-2-Dimethyl-5-(arylmethylene)
1,3-dioxane-4,6-diones 21a-b     25
1.10    Palladium-Catalyzed Propargylallylation of Dienes 23a-c with Allylic Chlorides 5a-c and Allenylstannanes 12a     26
1.11    Synthesis of Activated Dienes 23a-c     28
1.12    Possible mechanism for Propargylallylation of Activated Olefins     31
1.13    Support for Involvement of □-Allyl Palladium Intermediate 24 in the present catalytic reaction     32
1.14    Support for Six-Membered Cyclic Transition State by Deuterated studies     33
1.15    Support for Six-Membered Cyclic Transition State     35

Chapter 2

2.1    Palladium-Catalyzed addition reactions of Allylic
Chlorides 5a-e and Alkynylstannanes 12a-i with
Benzyne Precursor 1a-d     72
2.2    Preparation of the Aryne Precursor 1a-f     73
2.3    Preparation of Substituted 2-Bromophenol     75
2.4    Synthesis of Substituted Alkynylstannanes 12a-i     75
2.5    Effects on the Leaving Group of the Allylic Substrates     77
2.6    Palladium-Catalyzed addition reactions of Allylic Chlorides 5a-e, and Allenylstannanes 19a-c with Benzyne Precursor 1a-e     82
2.7    Deuterium-Labeling Study of Allenyltributylstannane 19b     83
2.8    Synthesis of (Tributylstannyl)-1,2-butadiene 19c     84
2.9    Palladium-Catalyzed addition reactions of Allylic Chlorides 5a-e and Alkynylstannanes 21a-c with Benzynes Precursor 1a-e     86
2.10    Synthesis of (E)-2-Phenyl-1-vinylstannane 21c     87
2.11    Applications of 1-Allyl-2-alkynyl benzenes 18b, j and k     89
2.12    Possible Mechanism for Allylalkynyl, Allylallenyl, and Allylalkenylation of Benzynes
     91
2.13    Support for the Involvement of □-Allyl Palladium Intermediate 25     92
2.14    Support for the Involvement of Benzyne in present catalytic reactions     93
2.15    Support for Palladium Intermediate 28 in present Benzyne reactions     95

Chapter 3

3.1    Palladium-Catalyzed addition reactions of Aryl Iodides and 15a-h Stannylgermanes 25h with Allenes 6a-d     134
3.2    Synthesis of Allenes 6a-d     135
3.3    Preparation of Tributylstannyltrimethylgermane 25h     136
3.4    Palladium-Catalyzed addition reactions of Iodoallenes 20a-j and Stannylgermanes 25h     141
3.5    Synthesis of substituted
1-Iodo-2-allenyloxymethylbenzene 20a-e     142
3.6    Synthesis of N-(o-Iodobenzyl)-N-(phenylsulfonyl)
-1,2-propadienylamine 20f-j     143
3.7    Palladium-Catalyzed addition reactions of Iodoallenes 20a-j and Stannylsilanes 25a     146
3.8    Possible mechanism for addition reactions of Aryl Iodides and Stannylgermanes with Allenes     149
3.9    Possible Mechanism for the addition reactions of Stannylgermanes to Iodoallenes     152

Chapter 4

4.1    Palladium-Catalyzed Silylstannantion 10a-b of Allenes 1a-k     181
4.2    Preparation of Allenes 1a-h     182
4.3    Determination of Stereochemistry of Products 11 Based on the NOE Studies     185
4.4    Possible Mechanism for the Palladium-Catalyzed Silylstannantion of Allenes     187
List of Tables

Table 1
        Page
1.1    Effects of Catalysts, Allyl Halides 5 and Solvents on the Propargylallylation of Malononitrile 6a with Allyl Halide 5 and Allenylstannane 12a     13
1.2    Palladium-Catalyzed Propargylallylation of Malononitriles 6a-g with Allylic Chlorides 5a-e and Allenylstannane 12a     15
1.3    Palladium-Catalyzed Propargylallylation of Indanediones 19a-j with Allylic Chlorides 5a-b, d-e and Allenylstannane 12a     21
1.4    Palladium-Catalyzed Propargylallylation of Substituted 2-2-Dimethyl-5-(arylmethylene)-1,3-dioxane-4,6-diones
21a-b with Allylic Chlorides 5a-b, d and Allenylstannane 12a     26
1.5    Palladium-Catalyzed Propargylallylation of Dienes 23a-c with Allylic Chlorides 5a-b, d and Allenylstannane 12a     29

Table 2

2.1    Effects of Catalysts, Allyl Halides CH2=CHCH2X, and Solvents on the Allylalkynylation of Benzyne 1a with Allyl Halide 5 and Alkynylstannane 12a     78
2.2    Palladium-Catalyzed Allylalkynylation of Benzynes 1a-d
with Allylic Chlorides 5a-e and Alkynylstannanes 12a-i     80
2.3    Palladium-Catalyzed Allylallenylation of Benzynes 1a-e with Allylic Chlorides 5a-e and Allenylstannanes 19a-c     86
2.4    Palladium-Catalyzed Allylalkenylation of Benzynes 1a-d with Allylic Chlorides 5a-e and Alkenylstannanes 21a-c     88
2.5    Palladium-Catalyzed Multiple-Ring Formation of 1,6-Enynes 18b, 18j and 18k with Aromatic Iodides 23a-b     90

Table 3

3.1    Effects of Catalysts and Solvents on the three component assembling of 4-Methoxy Aryl Iodide 15a, Allenes 6a, and Stannylgermanes 25h     137
3.2    Palladium-Catalyzed three component assembling of Aryl Iodides 15a-h with Allenes 6a-d and Stannylgermanes 25h     139
3.3    Effects of Solvents on the reaction of 1-Iodo-2-allenyloxymethylbenzene 20a and Stannylgermanes 25h     144
3.4    Palladium-Catalyzed Partially Intermolecular Coupling reactions of Substituted Iodoallenes 20a-j and Stannylgermane 25h     145
3.5    Palladium-Catalyzed Partially Intermolecular Coupling reactions of Substituted Iodoallenes 20a-j and Stannylgermane 25a     148



Table 4

4.1    Effects of Catalysts and Solvents on the addition reaction of Allene 1a, and Silylstannane 10a     183
4.2    Palladium-Catalyzed addition reactions of Allenes 1, and Silylstannanes 10a-b     185

                                

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