Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features

Longcheng Hong; Weijia Lin; Fangjun Zhang; Ruiting Liu; Xigeng Zhou

doi:10.1039/c3cc42534g

Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features

Chem Commun (Camb). 2013 Jun 21;49(49):5589-91. doi: 10.1039/c3cc42534g.

Authors

Longcheng Hong¹, Weijia Lin, Fangjun Zhang, Ruiting Liu, Xigeng Zhou

Affiliation

¹ Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200433, People's Republic of China.

PMID: 23676902
DOI: 10.1039/c3cc42534g

Abstract

The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mechanistic features involving a tandem anionic cascade cyclization and anti-addition across the C≡C triple bond.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Azides / chemistry*
Catalysis
Cyclization
Lanthanoid Series Elements / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Triazoles / chemical synthesis*
Triazoles / chemistry

Substances

Alkynes
Azides
Lanthanoid Series Elements
Organometallic Compounds
Triazoles