Regioselective umpolung addition of dicyanobenzene to α,β-unsaturated alkenes enabled by electrochemical reduction?

Organic Chemistry Frontiers Pub Date: 2022-01-11 DOI: 10.1039/D1QO01852C

Abstract

An umpolung addition of dicyanobenzene to α,β-unsaturated alkenes has been developed using an electroreductive strategy. This electrochemical protocol is well compatible with a broad range of conventionally challenging substrates, including α,β-unsaturated esters, nitriles and trisubstituted enones. Moreover, good to excellent regioselectivities are observed in the reaction of cinnamates with dicyanobenzene. Synthetic utility of this electrochemical approach is further demonstrated by direct late-stage functionalization of (S)-verbenone and 16-dehydropregnenolone acetate.

Graphical abstract: Regioselective umpolung addition of dicyanobenzene to α,β-unsaturated alkenes enabled by electrochemical reduction
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