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

页码：4912 / 4915

页数：4

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