Ruthenium-catalyzed dipolar cycloaddition of organic azides and alkynes

ORGN 365

Brant Boren, bcboren@scripps.edu1, Sridhar Narayan, sridharn@scripps.edu1, Lars K. Rasmussen1, Guochen Jia, chjiag@ust.hk2, and Valery V. Fokin1. (1) Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, (2) Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China

Ru(II) complexes, such as Cp*RuCl(PPh3)2, regioselectively catalyze 1,3-dipolar cycloaddition of organic azides and alkynes. Diversely functionalized 1,5-disubstituted triazoles are usually obtained in good to excellent yield after heating the reaction mixture at 50 – 80 oC for several hours. Furthermore, internal alkynes also participate in the catalysis, producing 1,4,5-trisubstituted 1,2,3-triazoles. Thus, the ruthenium system complements the copper-catalyzed azide-alkyne cycloaddition, providing facile access to wide range of 1,2,3-triazoles with different substitution patterns.