title: Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C-C Bond Activation.
abstract: A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon-carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid substrates, providing good to excellent yields of the new ketones, particularly those containing electron-withdrawing substituents. Catalyst reactivity is dependent on quinolinyl ketone substrates, with alkyl ketones requiring Rh(PPh3)3Cl instead of the more reactive [Rh(C2H4)2Cl]2. With the use of K2CO3 as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique.
authors.affiliation: Department of Chemistry, Hope College , 35 East 12th Street, Holland, Michigan 49423, United States.
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Dennis
authors.affiliation: Department of Chemistry, Hope College , 35 East 12th Street, Holland, Michigan 49423, United States.
authors.forename: Chad T
authors.initials: CT
authors.lastname: Compagner
authors.affiliation: Department of Chemistry, Hope College , 35 East 12th Street, Holland, Michigan 49423, United States.
authors.forename: Stanna K
authors.initials: SK
authors.lastname: Dorn
authors.affiliation: Department of Chemistry, Hope College , 35 East 12th Street, Holland, Michigan 49423, United States.
authors.forename: Jeffrey B
authors.initials: JB
authors.lastname: Johnson