Base-Free Pd-Catalyzed C-Cl Borylation of Fluorinated Aryl Chlorides

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.

Automated summary

This study presents an efficient catalytic C-Cl borylation method for di-ortho-fluorinated aryl chlorides using a combination of Pd(dba)(2) and SPhos as ligand, conducted under base-free conditions. The resulting aryl boronate products are sensitive to base.