Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid

Clare E. Jacobson, Noelia Martinez-Muñoz and David J. Gorin*

*Department of Chemistry, Smith College, 100 Green Street, Northampton, Massachusetts 01063, United States, Email: dgorinsmith.edu

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

DOI: 10.1021/acs.joc.5b01077

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Abstract

A Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid proceeds in air as sole oxidant and offers a strategy for replacing toxic, electrophilic alkylating reagents. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.

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Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids

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

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Key Words

Chan-Lam coupling, esters, methyl esters

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ID: J42-Y2015