Alkenes as Azido Precursors for the One-Pot Synthesis of 1,2,3-Triazoles Catalyzed by Copper Nanoparticles on Activated Carbon.

F. ALONSO; Y. MOGLIE; G. RADIVOY; M. YUS

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2013 vol. 78 p. 5031 - 5037

0022-3263

A one-pot protocol for the synthesis of 1,2,3- triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon−carbon double bond and the copper-catalyzed azide− alkyne cycloaddition (CuAAC). High yields of the β- methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.