A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes
A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes
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DOI：
10.1021/jo061688m
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发表时间：
2006-10-27
影响因子：
3.6
通讯作者：
Weinreb, Steven M.
中科院分区：
文献类型：
--
作者：
Majireck, Max M.;Weinreb, Steven M.
研究了在Cp*RuCl(PPh_3)(2)催化下烷基叠氮化物与各种不对称内炔在回流苯中的[3+2]-环加成反应，得到了1，4，5-三取代-1，2，3-三氮唑。而烷基苯基和二烷基乙炔进行环加成反应得到区域异构体1，2，3-三唑的混合物，而酰基取代的内炔则具有完全的区域选择性。此外，还发现炔丙醇和炔丙胺与叠氮化合物反应生成单一的区域异构体。
[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.