CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1284-1292
DOI: 10.1055/s-0037-1611633
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Visible-Light-Induced Decarboxylative C–H Adamantylation of Azoles at Ambient Temperature

Julian Koeller
,
,
Institut für Organische und Biomolekulare Chemie, Georg August-Universität, Tammannstraße 2, 37077 Göttingen, Germany   Email: Lutz.Ackermann@chemie.uni-goettingen.de
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Further Information

Publication History

Received: 24 November 2018

Accepted: 27 November 2018

Publication Date:
19 December 2018 (online)


§ 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.

Supporting Information

 
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