Use of tunable ligands allows for intermolecular Pd-catalyzed C--O bond formation.
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.
Vorogushin
Andrei V
AV
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Huang
Xiaohua
X
Buchwald
Stephen L
SL
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008024:Ligands; D010165:Palladium / Q000737:chemistry
D000438:Alcohols; D004987:Ethers; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D010165:Palladium