Alumina-supported copper iodide: an efficient and recyclable catalyst for microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component reaction in water

TitleAlumina-supported copper iodide: an efficient and recyclable catalyst for microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component reaction in water
Publication TypeJournal Article
Year of Publication2015
AuthorsAgalave, SG, Pharande, SG, Gade, SM, Pore, VS
JournalAsian Journal of Organic Chemistry
Volume4
Issue9
Pagination943-951
Date PublishedSEP
ISSN2193-5807
Keywords1, 2, 3-triazoles, 4, copper(I) iodide, Cycloaddition, disubstituted 1, Microwave chemistry, supported catalysts
Abstract

A one-pot procedure for the synthesis of 1,4-disubstituted 1,2,3-triazoles by a three-component reaction of allyl or benzyl halides, sodium azide, and terminal alkynes over a neutral alumina-supported copper iodide catalyst has been developed. The products were isolated by simple filtration followed by washing of the catalyst with acetone. The products were obtained in almost pure form in up to 98% yield (TON 495). The catalyst can be recycled for more than eight subsequent reactions. The halides are directly converted into triazoles via in situ formation of azides and thus handling of hazardous azides can be avoided. The broad scope of this protocol is shown by the synthesis of a variety of diversely substituted 1,2,3-triazoles and also two-component azide-alkyne click reaction. The key features of this procedure are the use of water as a solvent, recyclability of the catalyst up to eight runs without appreciable loss of activity, and high yields of products. The catalyst has been fully characterized by FTIR, solid-state NMR and EDX spectroscopy, ESEM, TGA, and XRD.

DOI10.1002/ajoc.201500189
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.275

Divison category: 
Chemical Engineering & Process Development
Organic Chemistry