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.