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Synthesis 2009(20): 3519-3526  
DOI: 10.1055/s-0029-1217005
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© Georg Thieme Verlag Stuttgart ˙ New York

Cyclization of Diazoacetamides Catalyzed by N-Heterocyclic Carbene Dirhodium(II) Complexes

Luis F. R. Gomesa, Alexandre F. Trindadea, Nuno R. Candeiasb, Luís F. Veirosc, Pedro M. P. Goisb, Carlos A. M. Afonso*a
a CQFM, Centro de Química-Física Molecular, Institute of Nanosciences and Nanotechnology, Instituto Superior Técnico, 1049-001 Lisboa, Portugal
b iMed.UL, Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal
c CQE, Centro de Química Estrutural, Instituto Superior Técnico, 1049-001 Lisboa, Portugal
Fax: +351(21)8464455/7; e-Mail: carlosafonso@ist.utl.pt;
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Publication History

Received 23 July 2009
Publication Date:
15 September 2009 (online)

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Abstract

The axial coordination of N-heterocyclic carbene ligands onto dirhodium(II) complexes was examined, together with its role in the intramolecular C-H insertion reactions of α-diazoacetamides. The formation of a decarbonylated product occurs by a free-carbene mechanism in which the structures of the catalyst and the acetamide play a decisive role.

Key words

carbenoids - carbene complexes - catalysis - diazo compounds - rhodium

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