Copper-Catalyzed Petasis-Type Reaction: A General Route to α-Substituted Amides From Imines, Acid Chlorides, and Organoboron Reagents

• Published in: Journal of organic chemistry Vol. 77; no. 4; pp. 2013 - 2017
• Main Authors: Morin, Marie S. T, Lu, Yingdong, Black, Daniel A, Arndtsen, Bruce A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.02.2012; Amer Chemical Soc
• Subjects: Amides - chemical synthesis; B derivatives; Benzoates - chemistry; Boranes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper - chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Imines - chemistry; Lewis Bases - chemistry; Magnetic Resonance Spectroscopy; Molecular Structure; Organic chemistry; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Pyridines - chemistry; Science & Technology; BORONIC ACIDS; MANNICH REACTION; ROOM-TEMPERATURE; CROSS-COUPLING REACTIONS; N-TERT-BUTANESULFINYL; ASYMMETRIC ARYLATION; MULTICOMPONENT SYNTHESIS; ENANTIOSELECTIVE ADDITION; ARYLBORONIC ACIDS; MILD NUCLEOPHILES; Catalytic reaction; Chemical reagent; Nitrogen heterocycle; Organic boron compounds; Transition metal; Imine; Pyridine derivatives; Petasis reaction; Copper ion; Acyl chloride; Carboxamide; Boron Organic compounds; Organic borane; Copper; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo202339v

A copper-catalyzed Petasis-type reaction of imines, acid chlorides, and organoboranes to form α-substituted amides is described. This reaction does not require the use of activated imines or the transfer of special units from the organoboranes and represent a useful generalization of the Petasis reaction.