A New Reagent for Direct Difluoromethylation

被引：518

作者：

Fujiwara, Yuta ^{[1
]}

Dixon, Janice A. ^{[1
]}

Rodriguez, Rodrigo A. ^{[1
]}

Baxter, Ryan D. ^{[1
]}

Dixon, Darryl D. ^{[1
]}

Collins, Michael R. ^{[2
]}

Blackmond, Donna G. ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Pfizer Inc, La Jolla Labs, Dept Chem, San Diego, CA 92121 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 03期

关键词：

BIOLOGICAL EVALUATION; HETEROAROMATIC BASES; PRACTICAL SYNTHESIS; SUBSTITUTIONS; HETEROCYCLES; INHIBITORS; ANALOGS;

D O I：

10.1021/ja211422g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO2CF2H)(2), DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated pi-systems and thiols. Regiochemical comparisons suggest that the CF2H radical generated from the new reagent possesses nucleophilic character.

引用

页码：1494 / 1497

页数：4

共 25 条

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