Journal
TETRAHEDRON
Volume 61, Issue 4, Pages 797-802Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.11.064
Keywords
aminocarbonylation; carbon monoxide; amino acid; palladium; ionic liquid
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Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF6] or [bmim][BF4] (where bmim=1-butyl-3-methyl-imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity. (C) 2004 Elsevier Ltd. All rights reserved.
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