Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution

被引：176

作者：

Liu, Chao ^{[1
,2
]}

Wang, Xiaoqing ^{[1
,2
]}

Li, Zhaodong ^{[1
,2
]}

Cui, Lei ^{[1
,2
]}

Li, Chaozhong ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Collaborat Innovat Ctr Chem Life Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

[3] Ningbo Univ Technol, Sch Chem Engn, Ningbo 315016, Zhejiang, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 31期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; INTRAMOLECULAR SCHMIDT REACTION; C-H BONDS; OXIDATIVE DECARBOXYLATION; INDOLIZIDINES (-)-167B; ASYMMETRIC-SYNTHESIS; HIGHLY EFFICIENT; ARYL HALIDES; METAL-FREE; AZIDES;

D O I：

10.1021/jacs.5b06821

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO3 as the catalyst and (KS2O8)-S-2 as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH3CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific azidation.

引用

页码：9820 / 9823

页数：4

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