A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes |
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Authors: | Majireck Max M Weinreb Steven M |
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Institution: | Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA. |
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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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