Visible-Light-Induced Decarboxylative C–H Adamantylation of Azoles at Ambient Temperature

^§ These authors contributed equally to this work

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The visible-light-promoted oxidant-free decarboxylative C–H adamantylation of azoles was accomplished under ambient reaction conditions. The novel acridinium photocatalyst and cobalt synergistic catalysis enabled the C–H adamantylation under oxidant-free reaction conditions. This C–H adamantylation strategy proved viable for a wide range of substituted azoles, including benzothiazole, benzoxazole, and benzimidazoles as well as caffeine derivatives, providing an expedient access to 2-adamantyl-substituted azoles.

Key words

photocatalysis - C–H functionalization - decarboxylation - cobalt - acridinium salts - oxidant-free - adamantylation - azoles

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