Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction

被引：86
|
作者：
Zhang, Yongqiang [1 ]
Teuscher, Kevin B. [1 ]
Ji, Haitao [1 ]
机构：
[1] Univ Utah, Dept Chem, Ctr Cell & Genome Sci, Salt Lake City, UT 84112 USA
来源：
CHEMICAL SCIENCE | 2016年 / 7卷 / 03期
关键词：
C-H BONDS; FREE-RADICAL CARBAMOYLATION; CATALYSIS; FUNCTIONALIZATION; ACTIVATION; CYANATION; ARYLATION; ORGANOCATALYSIS; THERMOLYSIS; STRATEGY;
D O I：
10.1039/c5sc03640b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A photoredox reaction for cross-dehydrogenative coupling (CDC) was developed to C-alpha-arylate amides (alpha to nitrogen) and ethers using a variety of five-and six-membered electron-deficient heteroarenes. A unique decomposition mechanism of ammonium persulfate enhanced by photoexcited benzaldehydes was revealed. This benzaldehyde-mediated photoredox reaction proceeded smoothly with household 23 W CFL bulbs as the energy source under metal-free conditions, allowing the construction of new C-sp(2)-C-sp(2) and C-sp(3)-C-sp(2) bonds and access to important pharmacophores of broad utility using commercially available reagents.
引用
收藏
页码：2111 / 2118
页数：8
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