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

Max M. Majireck, Steven M. Weinreb

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Abstract

[3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of Cp*RuCl(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.

Original languageEnglish (US)
Pages (from-to)8680-8683
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number22
DOIs
Publication statusPublished - Oct 27 2006

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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