Palladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and N-Methyl-N-methoxycarbamoyl Chloride

• Published in: Journal of organic chemistry Vol. 75; no. 4; pp. 1251 - 1258
• Main Authors: Krishnamoorthy, Ravi, Lam, Sang Q, Manley, Christopher M, Herr, R. Jason
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.02.2010; Amer Chemical Soc
• Subjects: Alkenes - chemistry; Amides - chemistry; Boronic Acids - chemistry; Carbamates - chemistry; Catalysis; Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; Kinetics and mechanisms; Magnetic Resonance Spectroscopy; Molecular Structure; Organic chemistry; Palladium; Physical Sciences; Reactivity and mechanisms; Science & Technology; Stereoisomerism; Structure-Activity Relationship; ARYL BROMIDES; KETONES; DESIGN; CONVENIENT METHOD; DIRECT CONVERSION; 2+2+2 COCYCLIZATION; AMINOCARBONYLATION; INHIBITORS; CARBOXYLIC-ACIDS; DIYNES; Catalytic reaction; Potassium compound; Palladium complex; Organic chlorine compounds; Chemical coupling; Unsaturated compound; Cross reaction; Carboxamide; Benzenic compound; Benzamide derivatives; Boron Organic compounds; Aromatic compound; Chemical synthesis; Ethylenic compound; Heterocyclic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo902647h

A simple protocol for the synthesis of Weinreb benzamides and α,β-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.