title: Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.
abstract: A variety of bicyclicN,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermolecular version employing 3-hexyne andN-cyanopyrrolidine also afforded the desiredN,N-disubstituted 2-aminopyridine in good yield.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Stolley
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Maczka
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA.
authors.forename: Janis
authors.initials: J
authors.lastname: Louie
keywords: Alkynes; Carbenes; Cyanamides; Cycloaddition; Nickel