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Synlett 2009(3): 441-446  
DOI: 10.1055/s-0028-1087553
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I) Halide Catalyzed Three-Component Coupling Reaction of Aldehyde, Pyrrolidine and Stannyl- and Silylacetylene

Adam Shih-Yuan Lee*, Ge-An Chen, Yu-Ting Chang, Shu-Fang Chu
Department of Chemistry, Tamkang University, Tamsui, Taipei 25137, Taiwan
Fax: +886(2)26223830; e-Mail: adamlee@mail.tku.edu.tw;
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Publication History

Received 23 September 2008
Publication Date:
21 January 2009 (online)

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Abstract

An efficient three-component coupling reaction of aldehyde, pyrrolidine and tributylstannylacetylene or triphenylsilylacety-lene to generate propargylamines has been developed by using copper(I) halides as promoters.

Key words

three-component coupling reaction - propargylamine - tributylstannylacetylene - triphenylsilylacetylene

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5

Dialkyne 1: ¹H NMR (CDCl3): δ = 1.75-1.84 (m, 8 H), 2.62-2.66 (m, 8 H), 4.78 (s, 2 H), 7.25-7.38 (m, 6 H), 7.51-7.55 (m, 4 H). ¹³C NMR (CDCl3): δ = 23.4, 50.0, 59.1, 71.0, 76.3, 127.7, 128.0, 128.2, 138.5. MS: m/z = 368(56) [M], 298(base), 297(48), 228(46), 175(22), 105(60).