title: Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.
abstract: We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIIIcatalytic cycle.
authors.affiliation: Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Corey H
authors.initials: CH
authors.lastname: Basch
authors.affiliation: Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Jennie
authors.initials: J
authors.lastname: Liao
authors.affiliation: Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Jianyu
authors.initials: J
authors.lastname: Xu
authors.affiliation: Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Jacob J
authors.initials: JJ
authors.lastname: Piane
authors.affiliation: Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Mary P
authors.identifier: 0000-0002-1879-5257
authors.initials: MP
authors.lastname: Watson
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
chemical_list: D000588:Amines; D009532:Nickel