title: Palladium-catalyzed preparation of Weinreb amides from boronic acids and N-methyl-N-methoxycarbamoyl chloride.
abstract: A simple protocol for the synthesis of Weinreb benzamides and alpha,beta-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates.
authors.affiliation: Medicinal Chemistry Department, Albany Molecular Research, Inc., 26 Corporate Circle, P.O. Box 15098, Albany, New York 12212-5098, USA.
authors.forename: Ravi
authors.initials: R
authors.lastname: Krishnamoorthy
authors.forename: Sang Q
authors.initials: SQ
authors.lastname: Lam
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Manley
authors.forename: R Jason
authors.initials: RJ
authors.lastname: Herr
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000475:Alkenes; D000577:Amides; D001897:Boronic Acids; D002219:Carbamates; C549276:N-methyl-N-methoxycarbamoyl chloride; D010165:Palladium