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Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids

Yuan Ji, Jessica Sweeney, Jillian Zoglio and David J. Gorin*

*Department of Chemistry, Smith College, Northampton, Massachusetts 01063, Email: dgorinsmith.edu

Y. Ji, J. Sweeney, J. Zoglio, D. J. Gorin, J. Org. Chem., 2013, 78, 11606-11611.

DOI: 10.1021/jo401941v (free Supporting Information)


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Abstract

Dimethylcarbonate is a nontoxic and green methylating reagent. A base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids offers high selectivity for esterification and mild reaction conditions, that enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism via direct methyl transfer from dimethylcarbonate to the substrate.


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Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid

C. E. Jacobson, N. Martinez-Muņoz, D. J. Gorin, J. Org. Chem., 2015, 80, 7305-7310.


Key Words

alkylation, methyl esters


ID: J42-Y2013