Rh(III)-Catalyzed Alkylation of 8‑Methylquinolines with Oxabenzonorbornadienes

Herein, a concise Rh(III)-catalyzed
C(sp3)–H
alkylation of 8-methylquinolines with oxabenzonorbornadiene scaffolds
and other strained olefins has been disclosed. The retention of the
oxabenzonorbornadiene skeleton, broad substrate scope, and wide-ranging
functional group tolerance are the key features of the developed catalytic
methodology. Mechanistic studies revealed that the reaction does not
involve a radical pathway, and the five-membered rhodacycle is the
key intermediate. This is the first report on the C(sp3)–H alkylation of 8-methylquinolines with strained oxabenzonorbornadiene
scaffolds (with ring retention).