Publications > Mañas et al
Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2H-Indazoles.
1. Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Andrés M. del Río (IQAR), Facultad de Farmacia, Universidad de Alcalá, Alcalá de Henares, 28805 Madrid, Spain. 2. Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS), Ctra. De Colmenar Viejo, Km. 9.100, 28034 Madrid, Spain.
Abstract
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C-N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step. Further derivatization enables functionalization of the 3-alkenyl-2H-indazoles.
