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).