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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

Author:
YuThese authors contributed equally to this work., Jian, Sheng, Hui-Xiang, Wang, Shuo-Wen, Xu, Zhen-Hua, Tang, Shi, Chen, Shi-Lu
Source:
Chemical communications 2019 v.55 no.31 pp. 4578-4581
ISSN:
1364-548X
Subject:
aromatization, chemical bonding, cleavage (chemistry), hydrolysis, quinones
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.
Agid:
6369811