Reductive ortho C-H cyanoalkylation of aryl (heteroaryl) sulfoxides: a general approach to a-aryl(heteroaryl) nitriles
Reductive ortho C-H cyanoalkylation of aryl (heteroaryl) sulfoxides: a general approach to a-aryl(heteroaryl) nitriles
复制标题
芳基（杂芳基）亚砜的还原性邻位 C–H 氰烷基化：制备 α-芳基（杂芳基）腈的通用方法
DOI：
10.1039/c8qo00268a
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发表时间：
2018-06-07
影响因子：
5.4
通讯作者：
Peng, Bo
中科院分区：
文献类型：
--
作者：
Luo, Fan;Lu, Yu;Peng, Bo
A general protocol for the synthesis of a-aryl-and heteroaryl nitriles has been developed. Specifically, the simple treatment of a mixture of aryl(heteroaryl) sulfoxides and a-stannyl nitriles with an anhydride produces a diverse array of a-aryl(heteroaryl) nitriles. Notable features of this reaction include its remarkably low reaction temperature (-78 degrees C), superior functional group compatibility, and highly transformable products. A DFT mechanistic study indicates that a counter anion (OCOCF3 -) extracting the SnBu3 group from a nitrilium-sulfurane adduct promotes the rapid formation of a ketenimine-sulfonium salt, which undergoes a facile dearomative Claisen-type rearrangement to form the product.
