Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids

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 dimethylcarbonat...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (22), p.11606-11611
Main Authors: Ji, Yuan, Sweeney, Jessica, Zoglio, Jillian, Gorin, David J
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401941v