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McDonagh, C,O'Conghaile, P,Gebbink, RJMK,O'Leary, P
2007
June
Tetrahedron Letters
Electrostatic immobilisation of copper(I) and copper(II) bis(oxazolinyl)pyridine catalysts on silica: application to the synthesis of propargylamines via direct addition of terminal alkynes to imines
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copper(I) bis(oxazolinyl)pyridines electrostatic immobilisation propargylamine silica DIELS-ALDER REACTIONS ENANTIOSELECTIVE SYNTHESIS COMPLEXES
48
4387
4390
Copper(I) and copper(II) complexes of two bis(oxazolinyl)pyridines were immobilized on silica via electrostatic interactions. The catalytic activity of the immobilized catalysts in the direct addition of terminal alkynes to imines leading to propargylamines was investigated under a variety of reaction conditions. The performance of the immobilized catalysts compares very well with their homogeneous equivalents. When used in toluene, the catalysts could be recycled a number of times and maintained activity. This study is the first such report of the immobilization on silica in this manner of any bis(oxazolinyl)pyridine (pybox) complex. (c) 2007 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tetlet.2007.04.095
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