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

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)


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 languageEnglish
Pages (from-to)1156-1165
Number of pages10
JournalThe Journal of Organic Chemistry
Issue number3
Publication statusPublished - 7 Feb 2014

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)'. Together they form a unique fingerprint.

Cite this