title: Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid.
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.
authors.affiliation: Department of Chemistry, Smith College, 100 Green Street, Northampton, Massachusetts 01063, United States.
authors.forename: Clare E
authors.initials: CE
authors.lastname: Jacobson
authors.affiliation: Department of Chemistry, Smith College, 100 Green Street, Northampton, Massachusetts 01063, United States.
authors.forename: Noelia
authors.initials: N
authors.lastname: Martinez-Muñoz
authors.affiliation: Department of Chemistry, Smith College, 100 Green Street, Northampton, Massachusetts 01063, United States.
authors.forename: David J
authors.initials: DJ
authors.lastname: Gorin