Divergent Regioselective Csp(2)-H Difluoromethylation of Aromatic Amines Enabled by Nickel Catalysis

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 difl...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 19; pp. 3549 - 3554
Main Authors Gou, Quan, Chen, Qianqiong, Tan, Qujian, Zhu, Minghong, Huang, Huisheng, Deng, Mengjiao, Yi, Wei, He, Shuhua
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 20.05.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
POTENT
CARBONYLATION
PHENOLS
ANILINES
ALKYLATION
LIGAND
C-H ACTIVATION
BORYLATION
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01262