DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)

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 investig...

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Veröffentlicht in:	Journal of organic chemistry 2014-02, Vol.79 (3), p.1156-1165
Hauptverfasser:	Wang, Zheng-Lin, Li, Hong-Liang, Ge, Li-Shi, An, Xing-Lan, Zhang, Zi-Gang, Luo, Xiaoyan, Fossey, John S, Deng, Wei-Ping
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzoquinones - chemical synthesis Benzoquinones - chemistry Furans - chemical synthesis Furans - chemistry Molecular Structure Nitriles - chemical synthesis Nitriles - chemistry Oxidative Coupling Thiophenes - chemical synthesis Thiophenes - chemistry
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo4026034