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Synthesis 2009(24): 4203-4207  
DOI: 10.1055/s-0029-1217034
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Tandem Oxidative α-Tosyloxylation of Alcohols/Nucleophilic Addition of Azide/Copper-Catalyzed 1,3-Dipolar Cycloaddition

P. Surendra Reddy, B. Sreedhar*
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: sreedharb@iict.res.in;
Further Information

Publication History

Received 7 July 2009
Publication Date:
12 October 2009 (online)

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Abstract

An efficient method is described for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles (β-keto-1,2,3-tria­zoles) in good to excellent yields by the successive treatment of secondary alcohols with [hydroxy(tosyloxy)iodo]benzene (Koser’s reagent, HTIB), sodium azide followed by copper(I) iodide catalyzed 1,3-dipolar cycloaddition with terminal alkynes.

Key words

β-keto-1,2,3-triazoles - 1,3-dipolar cycloaddition - secondary alcohols - α-tosyloxylation - copper iodide - terminal alkynes

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