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Synlett 2009(17): 2844-2848  
DOI: 10.1055/s-0029-1217982
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium N-Heterocyclic Carbene Complexes as Effective Catalysts for [2+2+2]-Cycloaddition Reactions

Iván González, Anna Pla-Quintana, Anna Roglans*
Department of Chemistry, University of Girona, Campus de Montilivi, s/n. 17071 Girona, Spain
Fax: +34(972)418150; e-Mail: anna.roglans@udg.edu;
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Publikationsverlauf

Received 1 July 2009
Publikationsdatum:
24. September 2009 (online)

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Abstract

Rhodium complexes of N-heterocyclic carbenes (NHC) [RhCl(cod)(NHC)], [cod = 1,5-cyclooctadiene, NHC = 1,3-diisopropylimidazolin-2-ylidene, and NHC = 1,3-dimesitylimidazolin-2-ylidene] are tested for intra- and partially intramolecular [2+2+2]-cycloaddition reactions demonstrating their effectiveness in this kind of process. This is the first use of a rhodium-NHC complex in a [2+2+2]-cycloaddition reaction of three alkynes. ESI-MS has been used to detect oxidative addition intermediates using rhodium NHC as the catalytic system.

Key words

cycloadditions - rhodium - carbenes - homogenous catalysis - polycycles

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