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Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid
Clare E Jacobson1, Noelia Martinez-Muñoz1, David J Gorin1
1Department of Chemistry, Smith College, 100 Green Street, Northampton, Massachusetts 01063, United States.
Abstract:
The oxidative coupling of alkylboronic acids with oxygen nucleophiles offers a strategy for replacing toxic, electrophilic alkylating reagents. Although the Chan-Lam reaction has been widely applied in the arylation of heteroatom nucleophiles, O-alkylation with boronic acids is rare. We report a Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid that proceeds in air with no additional oxidant. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.
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