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Copper-Catalyzed gem-Difluoroolefination of Diazo Compounds with TMSCF3 via C-F Bond Cleavage

Mingyou Hu, Zhengbiao He, Bing Gao, Lingchun Li, Chuanfa Ni and Jinbo Hu*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China, Email:

M. Hu, Z. He, B. Gao, L. Li, C. Ni, J. Hu, J. Am. Chem. Soc., 2013, 135, 17302-17305.

DOI: 10.1021/ja409941r (free Supporting Information)


A Cu-catalyzed gem-difluoroolefination of diazo compounds with TMSCF3 affords the desired 1,1-difluoroalkene products via trifluoromethylation followed by C-F bond cleavage.

see article for more examples

gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors

M. Hu, C. Ni, L. Li, Y. Han, J. Hu, J. Am. Chem. Soc., 2015, 137, 14496-14501.

Difluoromethyl 2-Pyridyl Sulfone: A New gem-Difluoroolefination Reagent for Aldehydes and Ketones

Y. Zhao, W. Huang, L. Zhu, J. Hu, Org. Lett., 2010, 12, 1444-1447.

Key Words

olefination, vinyl fluorides

ID: J48-Y2013