Copper(I)-Promoted Alkylation of Alkenylbenzyldimethylsilanes
Copper(I)-Promoted Alkylation of Alkenylbenzyldimethylsilanes
复制标题
DOI：
10.1002/ajoc.201402060
复制
发表时间：
2014-08-01
影响因子：
2.7
通讯作者：
Tsubouchi, Akira
中科院分区：
文献类型：
--
作者：
Takeda, Takeshi;Matsumura, Ryo;Tsubouchi, Akira
钯催化的酸碱不稳定杂原子功能化有机硅烷与C(sp(2))- x亲电试剂如芳基和烯基（伪）卤化物的交叉偶联已经得到了广泛的研究。相比之下，对于未活化的烯基三烷基硅烷与C(sp(3)) X亲电试剂之间的偶联知之甚少。本文描述了铜(I)促进的色谱稳定的烯基苄基二甲基硅烷与不反应的烷基卤化物以及烯丙基和苄基卤化物的偶联。该反应在CuI-P(OEt)(3)和Bu4NF中心点（tBuOH）(4)存在下进行，生成构型完全保留的立体二取代烯烃和三取代烯烃。
Palladium-catalyzed cross-coupling of acid- and base-unstable heteroatom-functionalized organosilanes and C(sp(2))-X electrophiles such as aryl and alkenyl (pseudo)halides has been extensively studied. In contrast, little is known about the coupling between unactivated alkenyltrialkylsilanes and C(sp(3)) X lectrophiles. Herein, the copper(I)-promoted coupling of chromatographically stable alkenylbenzyldimethylsilanes with unreactive alkyl halides as well as allyl and benzyl halides is described. The reaction proceeds in the presence of CuI-P(OEt)(3) and Bu4NF center dot(tBuOH)(4) to produce stereodefined di- and trisubstituted alkenes with complete retention of configuration.