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Mild C(sp3)‒H Alkylation of 8-Methylquinolines with α,β-Unsaturated Carbonyl Compounds by Rhodium(III) Catalysis

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A straightforward approach to the synthesis of γ-quinolyl carbonyl compounds has been presented via rhodium(III)-catalyzed C(sp3)-H alkylation of 8-methyquinolines with conjugated C=C multiple bonds. Remarkably, this C(sp3)-H functionalization proceeds under… Click to show full abstract

A straightforward approach to the synthesis of γ-quinolyl carbonyl compounds has been presented via rhodium(III)-catalyzed C(sp3)-H alkylation of 8-methyquinolines with conjugated C=C multiple bonds. Remarkably, this C(sp3)-H functionalization proceeds under mild reaction conditions, obviates the need for external oxidants, features high atom-economy, ample substrate scope and wide functional group tolerance. Mechanistic studies provided strong support for an irreversible C(sp3)‒H bond activation.

Keywords: alkylation methylquinolines; carbonyl compounds; sp3 alkylation; mild sp3; rhodium iii

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017

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