Synthesis 2015; 47(08): 1131-1146
DOI: 10.1055/s-0034-1379951
paper
© Georg Thieme Verlag Stuttgart · New York

2-Phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol as an Efficient and Versatile Auxiliary Ligand in Copper(II)-Catalyzed Buchwald–Hartwig and Sharpless–Meldal C–N Bond-Forming Reactions

Hashem Sharghi*
Department of Chemistry, Shiraz University, Shiraz, 71454, Iran   Email: [email protected]   Email: [email protected]
,
Pezhman Shiri*
Department of Chemistry, Shiraz University, Shiraz, 71454, Iran   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 02 September 2014

Accepted after revision: 02 December 2014

Publication Date:
17 February 2015 (online)


Abstract

A highly active, air-stable, and versatile procedure for Buchwald–Hartwig and Sharpless–Meldal C–N bond formation is reported. Under nearly solvent-free conditions using copper(II) acetate and 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol, a variety of N-heterocycles and various cyclic and noncyclic secondary amines were arylated to form N-aryl compounds in moderate to excellent yields. This methodology also provides rapid access to diverse 1,4-disubstituted 1,2,3-triazoles in good to excellent yields. All reactions are performed in short times under air.

Supporting Information

 
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