本文主要探討鈀金屬錯合物催化1,2-雙烯類化合物的加成反應，以及此類型反應在有機合成上的應用。研究主題分為兩大部分，第一部份是1,3-雙烯衍生物的新合成方法及利用p-allylpalladium錯合物進行親核置換反應而得到三分子偶合的產物。第二部份是將親電子試劑p-allylpalladium中間體的性質轉換成親核性試劑，然後攻擊羰基化合物如醛類、酮類化合物，進行羰基烯丙基化反應（carbonyl allylation）。
在第一部份中，以Pd(dba)2催化芳香基、烯基鹵化物與1,2-雙烯類化合物的加成反應，生成p-allylpalladium中間體，在鹼的存在下，進行去質子化（deportonation）反應可以得到1,3-雙烯衍生物；另外，若是反應中有親核性試劑如carboxylates或azide等陰離子，則會攻擊至所生成之p-allylpalladium中間體，而形成一新的鍵結，分別得到有機烯丙基酯化物（allylic carboxylates）及有機烯丙基疊氮化合物（allylic azides）。

在第二部份中，在PdCl2(PPh3)2的催化下，以SnCl2為還原劑及濃鹽酸水溶液（hydrochloric acid, 37 wt. % in water）為質子來源，促進1,2-雙烯類化合物與醛類分子進行羰基烯丙基化反應，可以得到具有高位向選擇性g-addition及高立體選擇性的homoallylic alcohol產物，反應是經由1,2-雙烯的hydrostannylation而生成三氯烯丙基錫試劑，再與醛類進行偶合反應而得到產物；另外，利用5 mol% PdCl2(PPh3)2為催化劑，加入10 mol%催化量的SnCl2以及2.5當量金屬還原劑鋅（Zn），在一毫升DMF的溶劑中，以烯丙醇為起始物與不同的醛類及酮類化合物進行羰基烯丙基化反應，得到homoallylic alcohols的衍生物。

Several new palladium-catalyzed addition reactions of allenes and their applications in organic synthesis are described. This thesis consists of two parts. The first part is concerned with new methodology to generate 1,3-butadiene derivatives and the three-component coupling reactions of nucleophilic substitution of p-allylpalladium complexes. The second part deals with the studies on the carbonyl allylation via apparent charge reversal of p-allylpalladium intermediate.
In the first part, a palladium-catalyzed reaction based on carbopalladation of allenes to generate a p-allylpalladium intermediate followed by deportonation of the resulting p-allylpalladium species was carried out to transfer allenes into substituted 1,3-butadienes. In addition to the synthesis of 1,3-butadienes, the p-allylpalladium species reacted with carboxylate and azide anions leading to the formation of allylic carboxylates and allylic azides, respectively.

In the second part, highly regio- and stereoselective allylation of aldehydes by allenes proceeds smoothly in aqueous/organic media in the presence of PdCl2(PPh3)2, HCl(aq), and SnCl2. The reaction occurs via hydrostannylation of allenes and allylation of aldehydes by the in situ generated allyltrichlorotins to afford the homoallylic alcohols. In addition, the allylation of carbonyl compounds by allylic alcohols via the formation and the apparent charge reversal of the p-allylpalladium complex in the catalytic system, 5 mol % PdCl2(PPh3)2, 10 mol % SnCl2, and excess Zn as metal reducing agent, gave the corresponding homoallylic alcohols.

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