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可见光促进的未活化三级膦与二芳基碘鎓盐的芳基化反应。

Catalyst-Free Arylation of Tertiary Phosphines with Diaryliodonium Salts Enabled by Visible Light.

机构信息

Department of Chemistry, M. V. Lomonosov Moscow State University, 119234, Moscow, Russia.

出版信息

Chemistry. 2019 Sep 25;25(54):12502-12506. doi: 10.1002/chem.201902955. Epub 2019 Sep 3.

Abstract

The visible-light-induced arylation of tertiary phosphines with aryl(mesityl)iodonium triflates to produce the quaternary phosphonium salts occurs under mild, metal, and catalyst-free conditions. Photo-excited EDA complexes between diaryliodonium salts and phosphines supposedly enable this transformation, which is difficult to achieve through the traditional ground-state reactions. Demonstrating high functional group tolerance, broad scope, and complete selectivity of the aryl group transfer, the method is particularly compatible with sterically congested phosphines, which are challenging under metal-based catalytic methods.

摘要

在温和的条件下,无需金属和催化剂,三芳基膦与芳基(均三甲苯基)碘𬭩三氟甲磺酸酯发生可见光诱导芳基化反应,生成季𬭸盐。据称,二芳基碘𬭩盐与膦之间的光致 EDA 配合物能够实现这种传统的基态反应难以实现的转化。该方法对芳基转移具有高的官能团容忍性、广泛的适用范围和完全的选择性,特别适用于空间位阻较大的膦,这在基于金属的催化方法中是具有挑战性的。

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