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

ABSTRACT: 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.

SUBMITTER: Budiman YP

PROVIDER: S-EPMC7986610 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Budiman Yudha P YP Lorenzen Sabine S Liu Zhiqiang Z Radius Udo U Marder Todd B TB

Chemistry (Weinheim an der Bergstrasse, Germany) 20210118 11

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)<sub>2</sub> (dba=dibenzylideneacetone) with SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) as a ligand is efficient to catalyze the C-Cl borylation of ...[more]

PMID: 33197081

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