Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

被引：28

作者：

Liang, Junqing ^{[1
]}

Hang, Jie ^{[1
]}

Wu, Jingjing ^{[1
]}

Wu, Pingjie ^{[1
]}

Hu, Jian ^{[1
]}

Hu, Feng ^{[1
]}

Wu, Fanhong ^{[1
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

中国国家自然科学基金;

关键词：

FLUORINATED GEM-DIOLS; ARYL BORONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; IODODIFLUOROMETHYL KETONES; RADICAL REACTION; ALKYL FLUORIDES; FACILE ACCESS; ARYLATION; MONOFLUOROMETHYLATION; INHIBITORS;

D O I：

10.1021/acs.orglett.9b02474

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalyzed coupling reaction of alpha-bromo-alpha-fluoroketones with arylboronic acids was reported, which provides an efficient pathway to access 2-fluoro-1,2-diary-lethanones in high yields. We also disclosed the synthesis of the monofluorination agents alpha-bromo-alpha-fluoroketones by using a trifluoroacetate release protocol. Mechanistic investigation indicated that a monofluoroalkyl radical is involved in the catalytic circle. Moreover, an important medical intermediate flindokalner was synthesized via a nickel-catalyzed coupling reaction of alpha-bromo-alpha-fluoro-2-indolone and boronic ester.

引用

页码：6844 / 6849

页数：6

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