Improved Process for the Palladium-Catalyzed C–O Cross-Coupling of Secondary Alcohols
Hong Zhang, Paula Ruiz‐Castillo, Alexander W. Schuppe, Stephen L. Buchwald
Abstract
An improved protocol for the Pd-catalyzed C–O cross-coupling of secondary alcohols is described. The use of biaryl phosphine L2 as the ligand was key to achieving efficient cross-coupling of (hetero)aryl chlorides with only a 20% molar excess of the alcohol. Additionally, we observed an unusual reactivity difference between an electron-rich aryl bromide and the analogous aryl chloride, and deuterium-labeling suggested that currently unidentified pathways for reduction play an important role in explaining this disparity.
Topics & Concepts
ChemistryArylPhosphinePalladiumBromideCatalysisReactivity (psychology)AlcoholLigand (biochemistry)ChlorideDeuteriumCombinatorial chemistryCoupling reactionMedicinal chemistryOrganic chemistryAlkylPathologyQuantum mechanicsMedicineAlternative medicineReceptorPhysicsBiochemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis