Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes
Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes
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DOI：
10.1021/jo4024057
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发表时间：
2014-01-03
影响因子：
3.6
通讯作者：
Nishihara, Yasushi
中科院分区：
文献类型：
--
作者：
Jiao, Jiao;Hyodo, Keita;Nishihara, Yasushi
通过高选择性过渡金属催化与炔基金属的同步二金属化反应，合成了一系列宝石和维二硼化乙烯基硅烷。该工艺可作为合成区域和立体多取代烯烃的通用方法。关键步骤是gem-和vici -二硼化乙烯基硅烷的非对映选择性Suzuki-Miyaura交叉偶联反应，其中两个硼基团表现出离散的反应活性，可以产生多种多取代烯烃前驱体。
The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.