Document Type
Article
Publication Date
10-18-2013
Publication Title
The Journal of Organic Chemistry
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.
Volume
78
Issue
22
First Page
11606
Last Page
11611
DOI
10.1021/jo401941v
Rights
“This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo401941v
Recommended Citation
Ji, Yuan; Sweeney, Jessica; Zoglio, Jillian; and Gorin, David J., "Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids" (2013). Chemistry: Faculty Publications, Smith College, Northampton, MA.
https://scholarworks.smith.edu/chm_facpubs/6
Comments
Peer reviewed accepted manuscript.