title: Benzoisothiazolone Organo/Copper-Cocatalyzed Redox Dehydrative Construction of Amides and Peptides from Carboxylic Acids using (EtO)3P as the Reductant and O2 in Air as the Terminal Oxidant.
abstract: Carboxylic acids and amine/amino acid reactants can be converted to amides and peptides at neutral pH within 5-36 h at 50 °C using catalytic quantities of a redox-active benzoisothiazolone and a copper complex. These catalytic "oxidation-reduction condensation" reactions are carried out open to dry air using O2 as the terminal oxidant and a slight excess of triethyl phosphite as the reductant. Triethyl phosphate is the easily removed byproduct. These simple-to-run catalytic reactions provide practical and economical procedures for the acylative construction of C-N bonds.
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Lanny S
authors.initials: LS
authors.lastname: Liebeskind
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Pavankumar
authors.initials: P
authors.lastname: Gangireddy
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Matthew G
authors.initials: MG
authors.lastname: Lindale
mesh_terms: D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003681:Dehydration; D010755:Organophosphates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D056831:Coordination Complexes; D010755:Organophosphates; D010455:Peptides; D013844:Thiazoles; D003300:Copper; C015699:1,2-benzisothiazoline-3-one; C009549:triethyl phosphate; D010100:Oxygen