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钯催化的烯丙基 C-OH 官能化反应用于高效合成功能化烯丙基硅烷。

Palladium-catalyzed allylic C-OH functionalization for efficient synthesis of functionalized allylsilanes.

机构信息

Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.

出版信息

J Am Chem Soc. 2011 Jan 26;133(3):409-11. doi: 10.1021/ja1096732. Epub 2010 Dec 16.

DOI:10.1021/ja1096732
PMID:21162529
Abstract

A new method is described for palladium-catalyzed allylic silylation using allylic alcohols and disilanes as precursors. The reactions proceed smoothly under mild and neutral conditions, and this method is suitable for synthesis of regio- and stereodefined allylsilanes. The presented silylation reaction can be easily extended to include synthesis of allylboronates by change of the dimetallic reagent. The presented synthetic procedure offers a broad platform for the selective synthesis of functionalized allyl metal reagents, which are useful precursors in advanced organic chemistry and natural product synthesis.

摘要

描述了一种新的钯催化烯丙基硅烷化方法,使用烯丙醇和二硅烷作为前体。该反应在温和中性条件下顺利进行,该方法适用于区域和立体选择性烯丙基硅烷的合成。所提出的硅烷化反应可以通过改变双金属试剂很容易地扩展到烯丙基硼酸酯的合成。所提出的合成方法为功能化烯丙基金属试剂的选择性合成提供了一个广泛的平台,这些试剂是先进有机化学和天然产物合成中有用的前体。

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