Palladium-Catalyzed Heck-Type Difluoroalkylation of Alkenes with Functionalized Difluoromethyl Bromides

被引：50
|
作者：
Zhang, Feng [1 ]
Min, Qiao-Qiao [1 ]
Zhang, Xingang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 19期
关键词：
alkenes; difluoroalkylation; functionalized difluoromethyl bromides; Heck-type reaction; palladium; COPPER-MEDIATED DIFLUOROMETHYLATION; ARYL BORONIC ACIDS; ALKYL-HALIDES; REDUCTIVE ELIMINATION; AMINO-ACIDS; CHLORIDES; IODIDES; TRIFLUOROMETHYLATION; DERIVATIVES; FLUORINE;
D O I：
10.1055/s-0035-1560457
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of difluoroalkylated alkenes through palladium-catalyzed Heck-type reaction with functionalized difluoromethyl bromides has been developed. The advantages of this protocol are its synthetic simplicity, excellent functional group compatibility, and efficient late-stage difluoroalkylation of biologically relevant molecules, thus paving a new way for application in drug discovery and development. Mechanistic studies revealed that the free difluoroalkyl radicals, initiated by a [Pd(0)L-n] via a single-electron-transfer (SET) pathway, were involved in the Heck-type catalytic cycle.
引用
收藏
页码：2912 / 2923
页数：12
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