title: Copper-catalyzed aerobic oxidation of hydroxamic acids leads to a mild and versatile acylnitroso ene reaction.
abstract: A mild formation of transient acylnitroso intermediates using a copper chloride catalyst and 1 atm of air as the terminal oxidant is described. The mild reaction conditions enable the inter- and intramolecular acylnitroso ene reaction with a wide range of functionalized alkene partners, as well as the first asymmetric variant. Notably, this transformation provides a practical and operationally simple method for effecting allylic amidation using an environmentally benign oxidant and a readily abundant transition metal.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA.
authors.forename: Charles P
authors.initials: CP
authors.lastname: Frazier
authors.forename: Jarred R
authors.initials: JR
authors.lastname: Engelking
authors.forename: Javier
authors.initials: J
authors.lastname: Read de Alaniz
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006877:Hydroxamic Acids / Q000737:chemistry*; D009603:Nitroso Compounds / Q000138:chemical synthesis*; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006877:Hydroxamic Acids; D009603:Nitroso Compounds; D016877:Oxidants; D003300:Copper