Organolanthanide-based synthesis of 1,2,3-triazoles from nitriles and diazo compounds

William J Evans; Elizabeth Montalvo; Timothy M Champagne; Joseph W Ziller; Antonio G DiPasquale; Arnold L Rheingold

doi:10.1021/ja077298e

Organolanthanide-based synthesis of 1,2,3-triazoles from nitriles and diazo compounds

J Am Chem Soc. 2008 Jan 9;130(1):16-7. doi: 10.1021/ja077298e. Epub 2007 Dec 8.

Authors

William J Evans¹, Elizabeth Montalvo, Timothy M Champagne, Joseph W Ziller, Antonio G DiPasquale, Arnold L Rheingold

Affiliation

¹ Department of Chemistry, University of California, Irvine, California 92697-2025, USA.

PMID: 18067300
DOI: 10.1021/ja077298e

Abstract

The reaction of [(C5Me5)2Ln][(mu-Ph)2BPh2] complexes with the lithium salt of (trimethylsilyl)diazomethane, Li[Me3SiCN2], gave products formulated as the dimeric isocyanotrimethylsilyl amide complexes {(C5Me5)2Ln[mu-N(SiMe3)NC]}2 (Ln = Sm, 1; La, 2). Reactions of (C5Me5)2Sm and [(C5Me5)2Sm(mu-H)]2 with Me3SiCHN2 also form 1. Complexes 1 and 2 react with Me3CCN to form the 1,2,3-triazolato complexes (C5Me5)2Ln(NCCMe3)[NNC(SiMe3)C(CMe3)N] (Ln = Sm, 3; La, 4). Complex 2 reacts with Me3SiN3 to make the isocyanide ligated azide complex {(C5Me5)2La[CNN(SiMe3)2](mu-N3)}3, 5.