Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Journal of organic chemistry, 2014-02, Vol.79 (3), p.1156-1165

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2014

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.