Copper-Catalyzed Reaction of Trifluoromethylketones with Aldehydes via a Copper Difluoroenolate

被引：67

作者：

Doi, Ryohei ^{[1
]}

Ohashi, Masato ^{[1
]}

Ogoshi, Sensuke ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 01期

关键词：

aldol reaction; boron; C-F activation; copper; synthetic methods; F BOND ACTIVATION; C-F; PHENOXIDE COMPLEXES; ALPHA-ARYLATION; ALDOL REACTIONS; ARYL BROMIDES; ALPHA; ALPHA-DIFLUOROKETONES; KETONES; ROUTE; DIFLUOROENOXYSILANES;

D O I：

10.1002/anie.201508266

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed reaction of easily accessible alpha,alpha,alpha-trifluoromethylketones with various aldehydes affords difluoro-methylene compounds in the presence of diboron and NaOtBu. The key process of the reaction is the formation of a copper difluoroenolate by 1,2-addition of a borylcopper intermediate to alpha,alpha,alpha-trifluoromethylketones and subsequent beta-fluoride elimination. Mechanistic studies including the isolation and characterization of a possible anionic copper alkoxide intermediate are also described.

引用

页码：341 / 344

页数：4

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