Journal
TETRAHEDRON
Volume 58, Issue 20, Pages 4015-4021Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00313-7
Keywords
carbon-carbon bond forming reactions; environmental benignity; fluorous phase; lanthanide; Lewis acid catalysis; tris(perfluoroalkanesulfonyl)methide; bis(perfluorooctanesulfonyl)amide
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Lanthanide tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide complexes are shown to be immobilized and continuously recycled in fluorous phases or as solids. The lanthanide complexes are thus extremely efficient Lewis acid catalysts for carbon-carbon bond forming (CCF) reactions. The CCF reactions such as the Friedel-Crafts acylation, Diels-Alder, and Mukaiyama aldol reaction are effectively catalyzed by the lanthanide complexes by virtue of the highly electron-withdrawing effect of tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide ponytails without any hydrocarbon spacer. (C) 2002 Published by Elsevier Science Ltd.
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