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Synfacts 2009(1): 0104-0104  
DOI: 10.1055/s-0028-1087257
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Propargylamines Catalyzed by PS-Supported NHC-Ag(I)

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
P. Li, L. Wang*, Y. Zhang, M. Wang
Huaibei Coal Teachers College, Anhui and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

A polystyrene-supported NHC-Ag(I) catalyst (PS-NHC-Ag(I)) 3 (0.78 mmol/g) was prepared via substitution of Merrifield resin 1 with benzylimidazole, followed by treatment with Ag2O. The three-component coupling of aldehydes 4, amines 5, and alkynes 6 took place in the presence of 3 (2 mol%; aldehyde:amine:alkyne = 1:1.1:1.1) under solvent-free conditions to give the corresponding propargylamines 7 in up to 98% yield (24 examples).