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Divergent Regioselective Csp2-H Difluoromethylation of Aromatic Amines Enabled by Nickel Catalysis.

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Herein, the first catalytic protocol for nickel-catalyzed ortho or para position difluoromethylation of various aromatic amines has been developed with the assistance of a bidentate phosphine ligand, offering an invaluable… Click to show full abstract

Herein, the first catalytic protocol for nickel-catalyzed ortho or para 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 p-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.

Keywords: divergent regioselective; difluoromethylation; aromatic amines; difluoromethylation aromatic; regioselective csp2; csp2 difluoromethylation

Journal Title: Organic letters
Year Published: 2022

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