Base‐Free Pd‐Catalyzed C−Cl Borylation of Fluorinated Aryl Chlorides
Please always quote using this URN: urn:nbn:de:bvb:20-opus-225687
- 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.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.…
Author: | Yudha P. Budiman, Sabine Lorenzen, Zhiqiang Liu, Udo Radius, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-225687 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Chemistry – A European Journal |
Year of Completion: | 2021 |
Volume: | 27 |
Issue: | 11 |
First Page: | 3869 |
Last Page: | 3874 |
Source: | Chemistry – A European Journal 2021, 27(11):3869-3874. DOI: 10.1002/chem.202004648 |
DOI: | https://doi.org/10.1002/chem.202004648 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Tag: | boronate ester; borylation; cross-coupling; fluoroarene; palladium-catalyzed |
Release Date: | 2021/10/27 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |