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2284032 
Journal Article 
DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene) 
Wang, Z; Li, HL; Ge, L; An, X; Zhang, ZiG; Luo, X; Fossey, JS; Deng, W 
2014 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
79 
3 
1156-1165 
24428373 
WOS:000331163800034 
A facile oxidative coupling of alpha-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available beta-diketones, simple ketones, and beta-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.