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

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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  The calculations were performed by using the Gaussian 98 package at the B3LYP/VDZP level for all molecules except 6′, where the B3PW91 functional was used. A full account of the computational details and a complete list of references are provided as Supporting Information.

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