title: Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.
abstract: For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Steven A
authors.initials: SA
authors.lastname: Rossi
authors.forename: Kirk W
authors.initials: KW
authors.lastname: Shimkin
authors.forename: Qun
authors.initials: Q
authors.lastname: Xu
authors.forename: Luis M
authors.initials: LM
authors.lastname: Mori-Quiroz
authors.forename: Donald A
authors.initials: DA
authors.lastname: Watson
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*
chemical_list: D000577:Amides; D001897:Boronic Acids; D016877:Oxidants; D010545:Peroxides; C111570:di-tert-butyl peroxide; D003300:Copper