DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)

Zheng Lin Wang; Hong Liang Li; Li Shi Ge; Xing Lan An; Zi Gang Zhang; Xiaoyan Luo; John S. Fossey; Wei Ping Deng

doi:10.1021/jo4026034

DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)

Zheng Lin Wang, Hong Liang Li, Li Shi Ge, Xing Lan An, Zi Gang Zhang, Xiaoyan Luo^*, John S. Fossey, Wei Ping Deng

^*Corresponding author for this work

Chemistry

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

56 Citations (Scopus)

Abstract

A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available β-diketones, simple ketones, and β-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.

Original language	English
Pages (from-to)	1156-1165
Number of pages	10
Journal	The Journal of Organic Chemistry
Volume	79
Issue number	3
DOIs	https://doi.org/10.1021/jo4026034
Publication status	Published - 7 Feb 2014

ASJC Scopus subject areas

Organic Chemistry

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title = "DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)",

abstract = "A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available β-diketones, simple ketones, and β-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.",

author = "Wang, {Zheng Lin} and Li, {Hong Liang} and Ge, {Li Shi} and An, {Xing Lan} and Zhang, {Zi Gang} and Xiaoyan Luo and Fossey, {John S.} and Deng, {Wei Ping}",

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doi = "10.1021/jo4026034",

language = "English",

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journal = "The Journal of Organic Chemistry",

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TY - JOUR

T1 - DDQ-mediated oxidative coupling

T2 - An approach to 2,3-dicyanofuran (thiophene)

AU - Wang, Zheng Lin

AU - Li, Hong Liang

AU - Ge, Li Shi

AU - An, Xing Lan

AU - Zhang, Zi Gang

AU - Luo, Xiaoyan

AU - Fossey, John S.

AU - Deng, Wei Ping

PY - 2014/2/7

Y1 - 2014/2/7

N2 - A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available β-diketones, simple ketones, and β-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.

AB - A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available β-diketones, simple ketones, and β-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.

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U2 - 10.1021/jo4026034

DO - 10.1021/jo4026034

M3 - Article

C2 - 24428373

AN - SCOPUS:84893858157

SN - 0022-3263

VL - 79

SP - 1156

EP - 1165

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 3

ER -

DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)

Abstract

ASJC Scopus subject areas

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