title: Catalytic methyl transfer from dimethylcarbonate to carboxylic acids.
abstract: Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and "green" potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols, and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.
authors.affiliation: Department of Chemistry, Smith College , Northampton, Massachusetts 01063.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Ji
authors.forename: Jessica
authors.initials: J
authors.lastname: Sweeney
authors.forename: Jillian
authors.initials: J
authors.lastname: Zoglio
authors.forename: David J
authors.initials: DJ
authors.lastname: Gorin