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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

22 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	10241-10247
頁數	7
期刊	Journal of Organic Chemistry
卷	83
發行號	17
DOIs	https://doi.org/10.1021/acs.joc.8b01443
出版狀態	已發佈 - 2018 9月 7

ASJC Scopus subject areas

有機化學

存取文件

10.1021/acs.joc.8b01443

其它文件與鏈接

CCDC 1835897: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Ichake, S. S. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator), Bandi, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1zmdhh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zmdhh&sid=DataCite
資料集: Dataset
CCDC 1825549: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Ichake, S. S. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator), Bandi, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1z8mpk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1z8mpk&sid=DataCite
資料集: Dataset
CCDC 1825548: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Ichake, S. S. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator), Bandi, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1z8mnj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1z8mnj&sid=DataCite
資料集: Dataset

引用此

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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\}",

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

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month = sep,

day = "7",

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

language = "English",

volume = "83",

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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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SP - 10241

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1835897: Experimental Crystal Structure Determination

CCDC 1825549: Experimental Crystal Structure Determination

CCDC 1825548: Experimental Crystal Structure Determination

引用此