Alkylation of Nonacidic C(sp3)-H Bonds by Photoinduced Catalytic Michael-Type Radical Addition

被引：63
|
作者：
Kamijo, Shin [1 ]
Takao, Go [1 ]
Kamijo, Kaori [1 ]
Tsuno, Teruo [2 ]
Ishiguro, Katsuya [1 ]
Murafuji, Toshihiro [1 ]
机构：
[1] Yamaguchi Univ, Grad Sch Sci & Technol Innovat, Yamaguchi 7538512, Japan
[2] Yamaguchi Univ, Dept Biol & Chem, Yamaguchi 7538512, Japan
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 19期
关键词：
AEROBIC PHOTOOXIDATIVE SYNTHESIS; SELECTIVE C-H; ELECTROPHILIC ALKENES; GEM-DIHYDROPEROXIDES; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; CYCLIC ETHERS; LIGHT;
D O I：
10.1021/acs.orglett.6b02391
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Photoinduced catalytic Michael-type radical addition was achieved via olefin insertion into a nonacidic C(sp(3))-H bond, utilizing 2-chloroanthraquinone as a C-H bond-cleaving catalyst and 1,1-bis(phenylsulfonyl)ethylene as an olefinic substrate. The present radical protocol allows carbon chain extension stemming from nonacidic C-H bonds, which complements alkylation at acidic C-H bonds under ionic conditions and installs the active methine site that acts as a versatile synthetic handle for further transformations.
引用
收藏
页码：4912 / 4915
页数：4
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