Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Copper-Catalyzed Radical Cascade Difluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes: A Route to Difluoromethylated Naphthoquinones

Copper-Catalyzed Radical Cascade Difluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes: A Route to Difluoromethylated Naphthoquinones
Gangguo Zhu, Mingming Ji, Yan Zhang, Dongmei Guo, Lisha Li, Shangyi Ye
A novel copper-catalyzed cascade difluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes has been developed. This method affords an efficient and straightforward access to structurally diverse difluoromethylated naphthoquinones in one pot, starting from readily available starting materials. The reaction represents the first trans-acyldifluoromethylation of internal alkynes, which features aldehydes as acceptors for the addition of alkenyl radicals. Furthermore, this protocol can also access to monofluoromethylated naphthoquinone and difluoromethylated indanones in the same reaction condition.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00964

DOI: 10.1021/acs.joc.7b00964

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