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

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, Steven M. Weinreb

Chemistry

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228 Scopus citations

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 language	English (US)
Pages (from-to)	8680-8683
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	71
Issue number	22
DOIs	https://doi.org/10.1021/jo061688m
State	Published - Oct 27 2006

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo061688m

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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.",

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N2 - [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.

AB - [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.

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

Abstract

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