Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN?

Organic Chemistry Frontiers Pub Date: 2022-06-06 DOI: 10.1039/D2QO00486K

Abstract

A novel and practical copper-catalyzed reaction for the 1,4-sulfonylcyanation of 1,3-enynes under mild conditions is described. This protocol provides efficient and straightforward access to a variety of 5-sulfonylpenta-2,3-dienenitrile derivatives with excellent functional group tolerance and good regioselectivity from readily available 1,3-enynes and commercially available sulfonyl chlorides and TMSCN. A mechanism involving sulfonyl and allenyl radical species is proposed.

Graphical abstract: Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN
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