Synthesis of Ketonylated Carbocycles via Excited-State Copper-Catalyzed Radical Carbo-Aroylation of Unactivated Alkenes.

ABSTRACT: Carbocycles are core skeletons in natural and synthetic organic compounds possessing a wide diversity of important biological activities. Herein, we report the development of an excited-state copper-catalyzed radical carbo-aroylation of unactivated alkenes to synthesize ketonylated tetralins, di- and tetrahydrophenanthrenes, and cyclopentane derivatives. The reaction is operationally simple and features mild reaction conditions that tolerate a broad range of functional groups. Preliminary mechanistic studies suggest a reaction pathway beginning with photoexcitation of [CuI-BINAP]₂ and followed by a single electron transfer (SET), radical aroylation of unactivated alkenes, radical cyclization, and re-aromatization, affording the desired ketonylated carbocycles.

SUBMITTER: Sarkar S 

PROVIDER: S-EPMC10723085 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature