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

[Image: see text] 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 cataly...

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Autores principales: Guzmán Ríos, David, Romero, Miguel A., González-Delgado, José A., Arteaga, Jesús F., Pischel, Uwe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10550203/
https://www.ncbi.nlm.nih.gov/pubmed/35337184
http://dx.doi.org/10.1021/acs.joc.2c00472
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author Guzmán Ríos, David
Romero, Miguel A.
González-Delgado, José A.
Arteaga, Jesús F.
Pischel, Uwe
author_facet Guzmán Ríos, David
Romero, Miguel A.
González-Delgado, José A.
Arteaga, Jesús F.
Pischel, Uwe
author_sort Guzmán Ríos, David
collection PubMed
description [Image: see text] 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.
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spelling pubmed-105502032023-10-05 Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex Guzmán Ríos, David Romero, Miguel A. González-Delgado, José A. Arteaga, Jesús F. Pischel, Uwe J Org Chem [Image: see text] 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. American Chemical Society 2022-03-25 /pmc/articles/PMC10550203/ /pubmed/35337184 http://dx.doi.org/10.1021/acs.joc.2c00472 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Guzmán Ríos, David
Romero, Miguel A.
González-Delgado, José A.
Arteaga, Jesús F.
Pischel, Uwe
Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title_full Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title_fullStr Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title_full_unstemmed Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title_short Metal-Mediated Organocatalysis in Water: Serendipitous Discovery of Aldol Reaction Catalyzed by the [Ru(bpy)(2)(nornicotine)(2)](2+) Complex
title_sort metal-mediated organocatalysis in water: serendipitous discovery of aldol reaction catalyzed by the [ru(bpy)(2)(nornicotine)(2)](2+) complex
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10550203/
https://www.ncbi.nlm.nih.gov/pubmed/35337184
http://dx.doi.org/10.1021/acs.joc.2c00472
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