Journal
CHEMCATCHEM
Volume 15, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202201128
Keywords
Copper Photoredox; Tetralin carbocycles; Unactivated alkenes; Aroyl Chlorides
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In this study, a new metal-catalyzed reaction was developed to synthesize ketonylated carbocycles with important biological activities. The reaction offers simple operation, mild reaction conditions, and tolerance towards various functional groups.
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 Cu catalyst and followed by a single electron transfer (SET), radical aroylation of unactivated alkenes, radical cyclization, and re-aromatization, affording the desired ketonylated carbocycles.
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