Visible-light initiated copper(i)-catalysed oxidative C–N coupling of anilines with terminal alkynes: one-step synthesis of α-ketoamides?

Green Chemistry Pub Date: 2014-11-06 DOI: 10.1039/C4GC01623H

Abstract

Development of C–N coupling processes is fundamentally important and challenging for the synthesis of biologically active molecules and drugs. Herein, we report a highly atom efficient green process for the synthesis of α-ketoamides via visible-light induced copper(I) chloride catalysed direct oxidative Csp–N coupling reactions using commercially available alkynes and anilines at room temperature without the use of hazardous chemicals and harsh reaction conditions. Forty-seven examples are presented using a broad range of substrates including electron deficient anilines and various terminal alkynes. The current photochemical process is able to achieve epoxide hydrolase inhibitors in one step with high yield (92–95%). This transformation is highly efficient and highly selective for the synthesis of α-ketoamides.

Graphical abstract: Visible-light initiated copper(i)-catalysed oxidative C–N coupling of anilines with terminal alkynes: one-step synthesis of α-ketoamides
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