Formation of β-cyano-ketones through cyanide-promoted ring-opening of cyclic organic carbonates?

Organic Chemistry Frontiers Pub Date: 2021-06-14 DOI: 10.1039/D1QO00770J

Abstract

Here we disclose a method for the unexpected decarboxylative cyanide-assisted ring-opening reaction of a series of vinyl cyclic carbonates. At elevated temperature, the attack of a cyanide nucleophile at the methylenic carbon center of the organic carbonate is promoted which leads to the release of CO2 and MeCN and the intermediacy of a Michael acceptor that undergoes facile 1,4-addition affording a β-cyano ketone product. This chemistry features a rare ring-opening reaction that is not initiated at the typically more electrophilic carbonate carbonyl.

Graphical abstract: Formation of β-cyano-ketones through cyanide-promoted ring-opening of cyclic organic carbonates
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