We herein describe the recent development of a series of highly diastereoselective Pd-catalyzed C-F bond activation of tetrasubstituted gem-difluoroalkenes in our laboratory. In the presence of catalytic tetrakis(triphenylphosphine)palladium(0), Sonogashira-type defluorinative coupling, hydrodefluorination (HDF) and base-free Suzuki-Miyaura cross-coupling of gem-difluoroalkenes can occur generating densely functionalized (E)-monofluoroalkenes with excellent diastereoselectivities (d.r. &gt;99:1). DFT calculations have elucidated an intriguing formal [4+1] cycloaddition/1,5-sigmatropic fluoride migration mechanism for the C-F bond activation process.

Stereoselective palladium-catalyzed C-F bond activation of tetrasubstituted gem-difluoroalkenes

ACS Fall 2021

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