Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy) 2 (nornicotine) 2 ] 2+ Complex.

Autor: Guzmán Ríos D; CIQSO─Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, Huelva E-21071, Spain., Romero MA; CIQSO─Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, Huelva E-21071, Spain., González-Delgado JA; CIQSO─Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, Huelva E-21071, Spain., Arteaga JF; CIQSO─Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, Huelva E-21071, Spain., Pischel U; CIQSO─Center for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, Huelva E-21071, Spain.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2022 Apr 15; Vol. 87 (8), pp. 5412-5418. Date of Electronic Publication: 2022 Mar 25.
DOI: 10.1021/acs.joc.2c00472
Abstrakt: The [Ru(bpy) 2 (Nor) 2 ] 2+ complex (Nor = nornicotine) is an efficient catalyst for the aldol reaction of acetone with activated benzaldehydes in a buffered aqueous solution. The metal plays the role of an activator for the nornicotine organocatalyst ligands. The resulting catalytic activity is potentiated by a factor of about 4.5 as compared to free nornicotine. Similar rate enhancements can be achieved by using Zn(II) cations as the activator. The observations are rationalized with the reduced basicity of the pyrrolidine N in nornicotine due to the enhanced electron withdrawal of the metal-complexed pyridyl moiety.
Databáze: MEDLINE
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