Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

被引：243

作者：

Song, Song ^{[1
]}

Sun, Xiang ^{[1
]}

Li, Xinwei ^{[1
]}

Yuan, Yizhi ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 12期

基金：

中国国家自然科学基金;

关键词：

C-H HALOGENATION; REGIOSELECTIVE HALOGENATION; CATALYTIC METHOD; FACILE SYNTHESIS; METHYL KETONES; STRATEGY; BOND; BROMIDE; ALKENES; ACCESS;

D O I：

10.1021/acs.orglett.5b00932

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

引用

页码：2886 / 2889

页数：4

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