Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction

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• 作者：Bieber ; Lothar W. ; da Silva ; Margarete F.
• 关键词：Aminomethylation ; Terminal alkynes ; Primary and secondary amines
• 刊名：Tetrahedron Letters
• 出版年：2004
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：November 1, 2004
• 卷：45
• 期：45
• 页码：8281-8283
• 文件大小：245 K

摘要

Terminal alkynes undergo mild and efficient aminomethylation with aqueous formaldehyde and secondary amines under CuI catalysis. In most cases high to nearly quantitative yields of tertiary propargylamines are obtained in DMSO solution at room temperature. Aromatic, aliphatic and silylated acetylenes as well as alkynols can be used. Primary amines are less reactive and satisfactory yields of secondary propargylamines are obtained only with phenylacetylene.