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

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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… Click to show full abstract

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).

Keywords: methodology; catalyzed alkylation; alkylation; alkylation methylquinolines; methylquinolines oxabenzonorbornadienes; iii catalyzed

Journal Title: Organic letters
Year Published: 2023

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