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

FRANCISCO ALONSO; YANINA MOGLIE; GABRIEL RADIVOY; MIGUEL 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 -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 the direct access to 1-vinyl and 4-monosubstituted triazoles.