title: Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.
abstract: Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of beta-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Vorogushin
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Huang
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008024:Ligands; D010165:Palladium / Q000737:chemistry
chemical_list: D000438:Alcohols; D004987:Ethers; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D010165:Palladium