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Cross-Coupling between Difluorocarbene and Carbene-Derived Intermediates Generated from Diazocompounds for the Synthesis of gem-Difluoroolefins

Jian Zheng, Jin-Hong Lin, Liu-Ying Yu, Yun Wei, Xing Zheng and Ji-Chang Xiao*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: jchxiaosioc.ac.cn

J. Zheng, J.-H. Lin, L.-Y. Yu, Y. Wei, X. Zheng, J.-C. Xiao, Org. Lett., 2015, 17, 6126-6129.

DOI: 10.1021/acs.orglett.5b03159 (free Supporting Information)


Abstract

A fast and practical cross-coupling between difluorocarbene and carbene-derived intermediates generated from diazocompounds provides hindered gem-difluoroolefins. Whereas the cross-coupling between difluorocarbene and aryl diazoacetates proceeded smoothly in the presence of a copper source, the coupling with diaryl diazomethanes occurred well under metal-free conditions.

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Key Words

difluoroolefins, vinyl fluorides


ID: J54-Y2015