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.
authors.affiliation: Shanghai Key Laboratory of New Drug Design & School of Pharmacy, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
authors.forename: Zheng-Lin
authors.initials: ZL
authors.lastname: Wang
authors.forename: Hong-Liang
authors.initials: HL
authors.lastname: Li
authors.forename: Li-Shi
authors.initials: LS
authors.lastname: Ge
authors.forename: Xing-Lan
authors.initials: XL
authors.lastname: An
authors.forename: Zi-Gang
authors.initials: ZG
authors.lastname: Zhang
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Luo
authors.forename: John S
authors.initials: JS
authors.lastname: Fossey
authors.forename: Wei-Ping
authors.initials: WP
authors.lastname: Deng
mesh_terms: D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D058451:Oxidative Coupling; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000591105:2,3-dicyanofuran; D016227:Benzoquinones; D005663:Furans; D009570:Nitriles; D013876:Thiophenes; C000928:dichlorodicyanobenzoquinone