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^*

^*Corresponding author for this work

Department of Chemistry

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

22 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 Sept 7

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b01443

Cite this

@article{3ed8f777010742fa899c38d195a161f4,

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\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "7",

doi = "10.1021/acs.joc.8b01443",

language = "English",

volume = "83",

pages = "10241--10247",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

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T1 - Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives

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

Y1 - 2018/9/7

N2 - 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.

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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UR - https://www.scopus.com/pages/publications/85050026056#tab=citedBy

U2 - 10.1021/acs.joc.8b01443

DO - 10.1021/acs.joc.8b01443

M3 - Article

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AN - SCOPUS:85050026056

SN - 0022-3263

VL - 83

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EP - 10247

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1825548: Experimental Crystal Structure Determination

CCDC 1835897: Experimental Crystal Structure Determination

CCDC 1825549: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 1825548: Experimental Crystal Structure Determination

CCDC 1835897: Experimental Crystal Structure Determination

CCDC 1825549: Experimental Crystal Structure Determination

Cite this