Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives

Bharath Kumar Villuri; Sachin S Ichake; Sabbasani Rajasekhara Reddy; Veerababurao Kavala; Vijayalakshmi Bandi; Chun-Wei Kuo; Ching-Fa Yao

doi:10.1021/acs.joc.8b01443

Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives

J Org Chem. 2018 Sep 7;83(17):10241-10247. doi: 10.1021/acs.joc.8b01443. Epub 2018 Jul 24.

Authors

Bharath Kumar Villuri¹, Sachin S Ichake¹, Sabbasani Rajasekhara Reddy^{1

2}, Veerababurao Kavala¹, Vijayalakshmi Bandi¹, Chun-Wei Kuo¹, Ching-Fa Yao¹

Affiliations

¹ Department of Chemistry , National Taiwan Normal University , 88, Section 4, Ting-Chow Road , Taipei 116 , Taiwan.
² Department of Chemistry, School of Advanced Sciences , Vellore Institute of Technology (VIT) , Vellore 632014 , India.

PMID: 29999313
DOI: 10.1021/acs.joc.8b01443

Abstract

The copper-catalyzed reaction of aryl aldehydes with 2-iodobenzylcyanides afforded 2-aryl-3-cyanobenzofurans in isolated yields of up to 74% in a cascade manner, which involves Knoevenagel condensation, aryl hydroxylation, oxa-Michael addition, and aromatization reactions. Conversely, 2-halo benzaldehydes as reacting partners with 2-iodobenzylcyanide regioselectively furnished dibenzo[ b,f]oxepine-10-carbonitrile derivatives up to 85% isolated yields via tandem Knoevenagel condensation, aryl hydroxylation, and Ullmann coupling reactions.