Issue 31, 2019

Copper-catalyzed radical cascades of para-quinone methides with AIBN and H2O via α-cyanoalkylation by C–C bond cleavage: new access to benzofuran-2(3H)-ones

Abstract

We describe the first one-pot construction of a benzofuran-2(3H)-one scaffold via a radical cascade reaction of para-quinone methides with azodiisobutyronitrile and water. In the presence of CuI (20 mol%), this cascade proceeds smoothly through 1,6-conjugate addition/aromatization, α-cyanoalkylation by unstrained and non-polar C(aryl)–C(t-butyl) bond cleavage, and downstream cyano-insertion/cyclization/hydrolysis, which leads to cyano-containing benzofuran-2(3H)-ones with an excellent functional-group compatibility.

Graphical abstract: Copper-catalyzed radical cascades of para-quinone methides with AIBN and H2O via α-cyanoalkylation by C–C bond cleavage: new access to benzofuran-2(3H)-ones

Supplementary files

Article information

Article type
Communication
Submitted
14 Jan 2019
Accepted
21 Mar 2019
First published
21 Mar 2019

Chem. Commun., 2019,55, 4578-4581

Copper-catalyzed radical cascades of para-quinone methides with AIBN and H2O via α-cyanoalkylation by C–C bond cleavage: new access to benzofuran-2(3H)-ones

J. Yu, H. Sheng, S. Wang, Z. Xu, S. Tang and S. Chen, Chem. Commun., 2019, 55, 4578 DOI: 10.1039/C9CC00294D

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