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

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)10241-10247
Number of pages7
JournalJournal of Organic Chemistry
Volume83
Issue number17
DOIs
Publication statusPublished - 2018 Sep 7

ASJC Scopus subject areas

  • Organic Chemistry

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