Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp2)-H and unactivated C(sp3)-H bonds

被引：58
作者：
Wu, Xuesong [1 ]
Zhao, Yan [1 ]
Ge, Haibo [1 ]
机构：
[1] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA
来源：
CHEMICAL SCIENCE | 2015年 / 6卷 / 10期
基金：
美国国家科学基金会;
关键词：
C-H BONDS; CATALYZED DIRECT THIOLATION; ELECTRON-DEFICIENT ARENES; BENZOIC-ACID DERIVATIVES; DIRECT ARYLATION; INTRAMOLECULAR AMINATION; DIRECTING GROUP; GENERAL-METHOD; FUNCTIONALIZATION; PALLADIUM;
D O I：
10.1039/c5sc02143j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The pyridine-enabled cross dehydrogenative coupling of sp(2) C-H bonds of polyfluoroarenes and unactivated sp(3) C-H bonds of amides was achieved via a copper-promoted process with good functional group compatibility. This reaction showed great site-selectivity by favoring the sp(2) C-H bonds ortho to two fluoro atoms of arenes and the sp(3) C-H bonds of a-methyl groups over those of the amethylene, b-or g-methyl groups of the aliphatic amides. Mechanistic studies revealed that sp(3) C-H bond cleavage is an irreversible but not the rate-determining step, and the sp(2) C-H functionalization of arenes appears precedent to the sp(3) C-H functionalization of amides in this process.
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页码：5978 / 5983
页数：6
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