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Copper-Catalyzed Coupling Cyclization of gem-Difluoroalkenes with Activated Methylene Carbonyl Compounds: Facile Domino Access to Polysubstituted Furans

Xuxue Zhang, Wenpeng Dai, Wei Wu and Song Cao*

*Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China, Email: scaoecust.edu.cn

X. Zhang, W. Dai, W. Wu, S. Cao, Org. Lett., 2015, 17, 2708-2711.

DOI: 10.1021/acs.orglett.5b01123 (free Supporting Information)


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Abstract

An efficient CuI-catalyzed coupling cyclization of gem-difluoroalkenes with active methylene carbonyl compounds such as 1,3-dicarbonyl compounds, acetoacetonitrile, and phenylsulfonylacetone enables the synthesis of 2,3,5-trisubstituted furans with the assistance of a base. Very good isolated yields, and excellent functional group compatibility make this transformation a powerful tool for the synthesis of various furans.


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Key Words

furans


ID: J54-Y2015