A Convenient Late-Stage Fluorination of Pyridylic C-H Bonds with N-Fluorobenzenesulfonimide

被引：57

作者：

Meanwell, Michael ^{[1
]}

Nodwell, Matthew B. ^{[1
]}

Martin, Rainer E. ^{[2
]}

Britton, Robert ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

[2] F Hoffmann La Roche Ltd, Roche Innovat Ctr Basel, Roche Pharma Res & Early Dev pRED, Med Chem, Grenzacherstr 124, CH-4070 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 42期

基金：

加拿大自然科学与工程研究理事会;

关键词：

fluorination; late-stage functionalization; medicinal chemistry; N-fluorobenzenesulfonimide; pyridines; BENZYLIC FLUORINATION; PHOTOCATALYTIC FLUORINATION; ELECTROPHILIC FLUORINATION; ANNULATED PYRIDINES; C(SP(3))-H BONDS; INHIBITORS; FLUORIDE; HETEROCYCLES; OMEPRAZOLE; REACTIVITY;

D O I：

10.1002/anie.201606323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pyridine features prominently in pharmaceuticals and drug leads, and methods to selectively manipulate pyridine basicity or metabolic stability are highly sought after. A robust, metal-free direct fluorination of unactivated pyridylic C-H bonds was developed. This convenient reaction shows high functional-group tolerance and offers complimentary selectivity to existing C-H fluorination strategies. Importantly, this late-stage pyridylic C-H fluorination provides opportunities to rationally modulate the basicity, lipophilicity, and metabolic stability of alkylpyridine drugs.

引用

页码：13244 / 13248

页数：5

共 58 条

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