Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes,Angewandte Chemie International Edition

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Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-07-17 , DOI: 10.1002/anie.201803541
Roman A. Novikov _{1,

2} , Denis D. Borisov ₁ , Anna V. Tarasova ₁ , Yaroslav V. Tkachev ₂ , Yury V. Tomilov ₁

Affiliation

A new strategy for the three‐component addition of halide anions and acetylenes to donor–acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1,2‐zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail.

中文翻译：

三组分镓（III）促进给体-受体环丙烷中卤化物阴离子和乙炔的添加

提出了一种新的策略，将卤化物阴离子和乙炔三组分添加到供体-受体环丙烷（DAC）中。镓（III）盐和DAC的1,2-两性离子反应性促进了以E选择性高的反应发生。它打开了涉及DAC的一组新流程。该反应容易在多种底物上发生，并且可以耐受各种官能团。这种方法使组装高度官能化的乙烯基卤化物成为可能，而后者是有机合成中非常方便的组成部分。详细讨论了该反应的可能机理及其立体化学方面。

更新日期：2018-07-17

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