α-Difluoromethylation on sp3 Carbon of Nitriles Using Fluoroform and Ruppert-Prakash Reagent

被引：36

作者：

Aikawa, Kohsuke ^{[1
]}

Maruyama, Kenichi ^{[1
]}

Honda, Kazuya ^{[1
]}

Mikami, Koichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

基金：

日本科学技术振兴机构;

关键词：

COPPER-MEDIATED DIFLUOROMETHYLATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; EFFICIENT PRECURSOR; ARYL; ACTIVATION; DIFLUOROCARBENE; CONSTRUCTION; ALDEHYDES; IMINES;

D O I：

10.1021/acs.orglett.5b02438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the alpha-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the alpha-siladifluoromethylated nitrile products, which can be utilized for sequential carbon carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.

引用

页码：4882 / 4885

页数：4

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