Alkylation of Nonacidic C(sp3)-H Bonds by Photoinduced Catalytic Michael-Type Radical Addition.
Photoinduced catalytic Michael-type radical addition was achieved via olefin insertion into a nonacidic C(sp3)-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.
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Shin
S
Kamijo
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Go
G
Takao
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Kaori
K
Kamijo
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Teruo
T
Tsuno
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Katsuya
K
Ishiguro
Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Toshihiro
T
Murafuji