Copper-catalyzed oxidative amidation of α,β-unsaturated ketones via selective C–H or C–C bond cleavage?

Organic Chemistry Frontiers Pub Date: 2017-04-24 DOI: 10.1039/C7QO00146K

Abstract

The copper-catalyzed oxidative amidation of readily available α,β-unsaturated ketones with N-fluorobenzenesulfonimide (NFSI) for the synthesis of biologically active enamides or α-amino substituted unsaturated ketone skeletons has been achieved. These transformations processed via a radical pathway, thus the amidation occurred at the unusual α-position of the α,β-unsaturated ketones, leading to the following effective C(CO)–C(vinyl) or C(vinyl)–H bond cleavage with high selectivity.

Graphical abstract: Copper-catalyzed oxidative amidation of α,β-unsaturated ketones via selective C–H or C–C bond cleavage
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