Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
Robert Szpera, Patrick G. Isenegger, Maxime Ghosez, Natan J. W. Straathof, Rosa Cookson, David C. Blakemore, Paul Richardson, Véronique Gouverneur
Abstract
Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [18F]trifluoroethanol.
Topics & Concepts
ChemistryArylCatalysisToluenePalladiumAlkylCoupling reactionFunctional groupCombinatorial chemistryCompatibility (geochemistry)Coupling (piping)Organic chemistryChemical engineeringPolymerMechanical engineeringEngineeringFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions