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

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

Research output: Contribution to journal › Article › peer-review

8 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 language	English
Pages (from-to)	10241-10247
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	83
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.8b01443
Publication status	Published - 2018 Sep 7

ASJC Scopus subject areas

Organic Chemistry

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Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives. / Villuri, Bharath Kumar; Ichake, Sachin S.; Reddy, Sabbasani Rajasekhara; Kavala, Veerababurao; Bandi, Vijayalakshmi; Kuo, Chun Wei; Yao, Ching Fa.

In: Journal of Organic Chemistry, Vol. 83, No. 17, 07.09.2018, p. 10241-10247.

Research output: Contribution to journal › Article › peer-review

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

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.",

author = "Villuri, {Bharath Kumar} and Ichake, {Sachin S.} and Reddy, {Sabbasani Rajasekhara} and Veerababurao Kavala and Vijayalakshmi Bandi and Kuo, {Chun Wei} and Yao, {Ching Fa}",

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AU - Villuri, Bharath Kumar

AU - Ichake, Sachin S.

AU - Reddy, Sabbasani Rajasekhara

AU - Kavala, Veerababurao

AU - Bandi, Vijayalakshmi

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2018/9/7

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AB - 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.

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