Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
(Chemical Equation Presented) A variety of diaryl ethers were synthesized by the Pd-catalyzed reaction of (hetero)-aryl halides and phenols. These reactions were achieved through the use of two new di-tert-butylphosphino biaryl ligands that overcome several limitations of previously described methods.
Burgos, Carlos H.,Barder, Timothy E.,Huang, Xiaohua,Buchwald, Stephen L.
p. 4321 - 4326
(2007/10/03)
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 β-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.,Huang, Xiaohua,Buchwald, Stephen L.
p. 8146 - 8149
(2007/10/03)
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