Exploring the regioselectivity of the cyanoalkylation of 3-aza-1,5-dienes: photoinduced synthesis of 3-cyanoalkyl-4-pyrrolin-2-ones?

Organic Chemistry Frontiers Pub Date: 2022-07-12 DOI: 10.1039/D2QO00918H

Abstract

A visible-light-induced regioselective cyanoalkylalkenylation of 1,5-dienes with oxime esters as the alkyl radical precursors is reported. Such a radical cascade proceeds with high yields and a broad substrate scope under mild conditions to provide 3-cyanoalkyl-4-pyrrolin-2-ones in one step from readily available N-vinylacrylamides. It is readily scalable to the gram scale, and could be induced by natural sunlight as a sustainable light source.

Graphical abstract: Exploring the regioselectivity of the cyanoalkylation of 3-aza-1,5-dienes: photoinduced synthesis of 3-cyanoalkyl-4-pyrrolin-2-ones
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