Base‐Free Pd‐Catalyzed C−Cl Borylation of Fluorinated Aryl Chlorides
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- 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.…
Autor(en): | Yudha P. Budiman, Sabine Lorenzen, Zhiqiang Liu, Udo Radius, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-225687 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Chemistry – A European Journal |
Erscheinungsjahr: | 2021 |
Band / Jahrgang: | 27 |
Heft / Ausgabe: | 11 |
Erste Seite: | 3869 |
Letzte Seite: | 3874 |
Originalveröffentlichung / Quelle: | Chemistry – A European Journal 2021, 27(11):3869-3874. DOI: 10.1002/chem.202004648 |
DOI: | https://doi.org/10.1002/chem.202004648 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | boronate ester; borylation; cross-coupling; fluoroarene; palladium-catalyzed |
Datum der Freischaltung: | 27.10.2021 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |