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无过渡金属 Zweifel 偶联反应合成功能化烯烃

Synthesis of Functionalized Alkenes by a Transition-Metal-Free Zweifel Coupling.

机构信息

School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.

出版信息

Org Lett. 2017 May 19;19(10):2762-2765. doi: 10.1021/acs.orglett.7b01124. Epub 2017 Apr 28.

DOI:10.1021/acs.orglett.7b01124
PMID:28453280
Abstract

The Zweifel reaction is a powerful method for the synthesis of alkenes, serving as a transition-metal-free alternative to the Suzuki-Miyaura reaction. To date, the scope of the Zweifel coupling has been rather narrow and has focused mainly on the coupling of vinyllithium reagents to synthesize simple aryl- and alkyl-substituted olefins. Herein, the development of a general transition-metal-free coupling process enabling the coupling of Grignard reagents or organolithiums is described. This method enables the enantiospecific synthesis of a wide variety of functionalized acyclic and cyclic olefin products.

摘要

泽维尔反应是一种合成烯烃的有力方法,它是铃木-宫浦反应的无过渡金属替代方法。迄今为止,泽维尔偶联的范围相当狭窄,主要集中在将乙烯基锂试剂偶联合成简单的芳基和烷基取代的烯烃上。本文描述了一种通用的无过渡金属偶联过程的发展,该过程能够实现格氏试剂或有机锂试剂的偶联。该方法能够对各种官能化的非环和环状烯烃产物进行对映选择性合成。

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