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Herein, the first catalytic protocol for nickel-catalyzed
or
position difluoromethylation of various aromatic amines has been developed with the assistance of a bidentate phosphine ligand, offering an invaluable synthesis means to construct extensive
-difluoromethylated products and difluorooxindole derivatives with significant functional fragments. Furthermore, the gram-scale reaction, broad substrate scope, excellent functional-group compatibility, late-stage difluoromethylation of pesticides, and even formal synthesis of HDAC6 inhibitors further demonstrate the usefulness of this method.