One pot ‘click’ reaction: CuII–hydrotalcite catalyzed tandem synthesis of β-hydroxy triazoles via regioselective opening of epoxide followed by [3+2] cycloaddition

Avvari N. Prasad; Boningari Thirupathi; Gangadhara Raju; Rapelli Srinivas; Benjaram M. Reddy

doi:10.1039/C2CY20052J

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One pot ‘click’ reaction: Cu^II–hydrotalcite catalyzed tandem synthesis of β-hydroxy triazoles via regioselective opening of epoxide followed by [3+2] cycloaddition†

Avvari N. Prasad,^a Boningari Thirupathi,^a Gangadhara Raju,^a Rapelli Srinivas^a and Benjaram M. Reddy*^a

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* Corresponding authors

^a Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad-500607, India
E-mail: bmreddy@iict.res.in, mreddyb@yahoo.com
Fax: +91 40 2716 0921
Tel: +91 40 27191714

Abstract

A novel copper (II) hydrotalcite catalyst has been investigated for its use in the cascade synthesis of β-hydroxy triazoles. It is found to be a dynamic catalyst for regioselective organic synthesis in water. The copper (II) hydrotalcite catalyst, in various Cu : Al molar ratios, was prepared by adopting a coprecipitation method and characterized using different techniques. The three component (epoxides, sodium azide and terminal alkynes) reactions under investigation were performed in water at ambient temperature without any additives. The formation of 2-azido alcohol, generated in situ, was observed to be the key step in the [3+2] cycloaddition of the click reaction. The optimized reaction procedures described herein are not only regioenriched and high yielding but also eco-friendly.

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Article information

DOI: https://doi.org/10.1039/C2CY20052J
Article type: Paper
Submitted: 29 Jan 2012
Accepted: 08 Mar 2012
First published: 09 Mar 2012

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Catal. Sci. Technol., 2012,2, 1264-1268

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One pot ‘click’ reaction: Cu^II–hydrotalcite catalyzed tandem synthesis of β-hydroxy triazoles via regioselective opening of epoxide followed by [3+2] cycloaddition

A. N. Prasad, B. Thirupathi, G. Raju, R. Srinivas and B. M. Reddy, Catal. Sci. Technol., 2012, 2, 1264 DOI: 10.1039/C2CY20052J

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