Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 22, Pages 11606-11611Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401941v
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Funding
- American Chemical Society Petroleum Research Fund [52706-UNI1]
- Smith College Provost's Office
- Smith College Provost's Science Center
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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.
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