Premium
Base‐Free Pd‐Catalyzed C−Cl Borylation of Fluorinated Aryl Chlorides
Author(s) -
Budiman Yudha P.,
Lorenzen Sabine,
Liu Zhiqiang,
Radius Udo,
Marder Todd B.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004648
Subject(s) - borylation , aryl , chemistry , catalysis , base (topology) , halide , fluorine , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , stoichiometry , organic chemistry , mathematics , mathematical analysis , biochemistry , alkyl , receptor
Catalytic C−X borylation of aryl halides containing two ortho ‐fluorines has been found to be challenging, as most previous methods require stoichiometric amounts of base and the polyfluorinated aryl boronates suffer from protodeboronation, which is accelerated by ortho ‐fluorine substituents. Herein, we report that a combination of Pd(dba) 2 (dba=dibenzylideneacetone) with SPhos (2‐dicyclohexylphosphino‐2’,6’‐dimethoxybiphenyl) as a ligand is efficient to catalyze the C‐Cl borylation of aryl chlorides containing two ortho ‐fluorine substituents. This method, conducted under base‐free conditions, is compatible with the resulting di ‐ortho ‐fluorinated aryl boronate products which are sensitive to base.