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. 2006 Oct 27;71(22):8680-3.
doi: 10.1021/jo061688m.

A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes

Max M Majireck  1 , Steven M Weinreb
Affiliations

A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes

Max M Majireck et al. J Org Chem. .

Abstract

[3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of CpRuCl(PPh3)2 as catalyst in refluxing benzene have been examined, leading to 1,4,5-trisubstituted-1,2,3-triazoles. Whereas alkyl phenyl and dialkyl acetylenes undergo cycloadditions to afford mixtures of regioisomeric 1,2,3-triazoles, acyl-substituted internal alkynes react with complete regioselectivity. In addition, propargyl alcohols and propargyl amines were found to react with azides to afford single regioisomeric products.

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Figures

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