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Catalytic cross-coupling of diazo compounds with coinage metal-based catalysts: an experimental and theoretical study. 2013

Ivan Rivilla, and W M C Sameera, and Eleuterio Alvarez, and M Mar Díaz-Requejo, and Feliu Maseras, and Pedro J Pérez
Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencias de los Materiales, Unidad Asociada al CSIC, Centro de Investigación en Química Sostenible (CIQSO), Universidad de Huelva, Campus de El Carmen s/n, 21007 Huelva, Spain.

We examined the ability of Tp(x)M (Tp(x) = hydrotris(pyrazolyl)borate ligand; M = Cu and Ag) and IPrMCl (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene; M = Cu, Ag, Au) complexes as catalyst precursors for the cross-coupling of diazo compounds. Experimental data showed that the metal centre can be tuned with the appropriate selection of the ligand to yield either the homo- or hetero-coupling (cross-coupling) products. A computational study of the reaction mechanism allowed the rationalization of the experimental reactivity patterns, and the identification of the key reaction step controlling the selectivity: the initial reaction between the metallocarbene intermediate and one of the diazo compounds.

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