Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Nickel-Catalyzed Defluorinative Reductive Cross-Coupling of gem-Difluoroalkenes with Unactivated Secondary and Tertiary Alkyl Halides

Nickel-Catalyzed Defluorinative Reductive Cross-Coupling of gem-Difluoroalkenes with Unactivated Secondary and Tertiary Alkyl Halides
Xiao-Xu Wang, Bin Xiao, Yao Fu, Tian-Jun Gong, Ben Zhang, Yan Wang, Xi Lu, Jing-Jing Pi
Herein, we described a nickel-catalyzed monofluoroalkenylation through defluorinative reductive cross-coupling of gem-difluoroalkenes with alkyl halides. Key to the success of this strategy is the combination of C–F cleavage with alkyl halides activation. This reaction enables the convenient synthesis of a large variety of functionalized monofluoroalkenes under mild reaction conditions with broad functional group compatibility and excellent Z-selectivity. The combination of Ni catalysis with (Bpin)2/K3PO4 as terminal reductant promoted the efficient C(sp2)–C(sp3) formation especially the generation of all-carbon quaternary centers with high chemoselectivity.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06469

DOI: 10.1021/jacs.7b06469

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