Copper‐Catalyzed Hydroxylation of Simple Fluoroaryl and Aryl Chlorides: A Route to (Fluoro)phenols
- 26 August 2026
- journal article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 29 (38)
Abstract
A copper‐catalyzed conversion of polyfluoroaryl chlorides to the corresponding phenols was developed. A simple ligand system was applied, as well as potassium carbonate as an inexpensive and effective base, while significantly suppressing competing S N Ar pathways. The generality of the method was further demonstrated with simple aryl chlorides, which also underwent efficient hydroxylation. Mechanistic studies suggest that the reaction proceeds via a Cu(I)/Cu(III) catalytic cycle. Notably, the use of a sulfolane/water solvent system enabled high reactivity at a low catalyst loading, underscoring the practicality and scalability of this protocol.Keywords
Funding Information
- Universität Heidelberg
This publication has 68 references indexed in Scilit:
- Ullmann Condensation Today: Arylation of Alcohols and Thiols with Aryl Halides2013
- Pd2dba3/Bippyphos: A Robust Catalyst System for the Hydroxylation of Aryl Halides with Broad Substrate ScopeAdvanced Synthesis & Catalysis, 2013
- Synthesis of Phenol, Aromatic Ether, and Benzofuran Derivatives by Copper‐Catalyzed Hydroxylation of Aryl HalidesAngewandte Chemie International Edition, 2009
- A Very Simple Copper‐Catalyzed Synthesis of Phenols Employing Hydroxide SaltsAngewandte Chemie International Edition, 2009
- Palladium‐Catalyzed Hydroxylation of Aryl Halides under Ambient ConditionsAngewandte Chemie International Edition, 2009
- Practical Imidazole‐Based Phosphine Ligands for Selective Palladium‐Catalyzed Hydroxylation of Aryl HalidesAngewandte Chemie International Edition, 2009
- Palladium Nanoparticles Supported on Polyaniline Nanofibers as a Semi‐Heterogeneous Catalyst in WaterAngewandte Chemie International Edition, 2007
- Palladium‐Catalyzed Coupling of Ammonia and Hydroxide with Aryl Halides: The Direct Synthesis of Primary Anilines and PhenolsAngewandte Chemie International Edition, 2007
- The Chemistry of Phenols2003
- Palladium-Catalyzed Coupling Reactions of Aryl ChloridesAngewandte Chemie International Edition, 2002