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DOI: 10.1055/s-2007-992511
Three-Component Coupling Reaction Using Silica-Immobilized CuI Catalyst
Contributor(s):Yasuhiro Uozumi, Hiroe TakenakaIndian Institute of Chemical Technology, Hyderabad and Jadavpur University, Kolkata, India
Silica-Immobilized CuI: An Efficient Reusable Catalyst for Three-Component Coupling Reaction of Aldehyde, Amine and Alkyne
Synlett 2007, 2301-2303
Publication History
Publication Date:
23 January 2008 (online)
Key words
three-component coupling - propargyl amines - silica - copper
Signifance
The three-component coupling of aldehydes, amines, and alkynes by using silica-immobilized CuI catalyst was described. Silica-supported copper catalyst SiO 2 -Py-CuI was prepared from 2-pyridylimine functionalized silica SiO 2 -Py with CuI in acetonitrile (eq. 1). The three-component coupling reactions of aldehydes, amines, and alkynes were carried out in the presence of 5 mol% silica-immobilized CuI catalyst SiO 2 -Py-CuI in acetonitrile at 90 °C to give the corresponding propargylamines in 54-93% yield (eq. 2).
Comment
Propargylamines are important synthetic intermediates for potential biologically active agents and polyfunctional amino derivatives. Previously, the authors reported hydroxyapatite-supported copper- (Tetrahedron Lett. 2004, 45, 7319) and layered double hydroxide supported gold-catalyzed three-component coupling reactions (Synlett 2005, 2329). The catalyst SiO 2 -Py-CuI was readily recovered by simple filtration and reused five times after washing and drying without any significant loss of catalytic activity.