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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Triphenylphosphine Dibromide: A Simple One-pot Esterification Reagent
Christophe Salomé1, Harold Kohn
1Division of Medicinal Chemistry and Natural Products, School of Pharmacy, and the Department of Chemistry University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7360.
Abstract:
We report a one-pot, expedient protocol for the conversion of carboxylic acids to their esters using excess triphenylphosphine dibromide, base, and the alcohol. The reaction gave the esterified product in moderate-to-high yields (30-95%). For chiral acids, the reaction proceeded with little or no racemization. Use of a chiral alcohol in this transformation gave the ester with retention of configuration of the stereogenic center. Information is presented indicating that esterification proceeds through the intermediate generation of an acyloxyalkoxyphosphorane and where steric interactions play an important role in the energetics of the reaction.
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