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Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis

Several group 11 metal complexes with chiral thiourea organocatalysts have been prepared and tested as organocatalysts. The promising results on the influence of metal‐assisted thiourea organocatalysts in the asymmetric Friedel–Crafts alkylation of indole with nitrostyrene are described. Better resu...

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Detalles Bibliográficos
Autores principales: Izaga, Anabel, Herrera, Raquel P., Gimeno, M. Concepción
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5485003/
https://www.ncbi.nlm.nih.gov/pubmed/28706568
http://dx.doi.org/10.1002/cctc.201601527
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author Izaga, Anabel
Herrera, Raquel P.
Gimeno, M. Concepción
author_facet Izaga, Anabel
Herrera, Raquel P.
Gimeno, M. Concepción
author_sort Izaga, Anabel
collection PubMed
description Several group 11 metal complexes with chiral thiourea organocatalysts have been prepared and tested as organocatalysts. The promising results on the influence of metal‐assisted thiourea organocatalysts in the asymmetric Friedel–Crafts alkylation of indole with nitrostyrene are described. Better results with the metal complexes have been achieved because of the cooperative effects between the chiral thiourea and the metal. The synergic effect between both species is higher than the effect promoted by each one separately, especially for gold(I). These outcomes are attributed to a pioneering gold(I) activation of the thiourea catalysts, affording a more acidic and rigid catalytic complex than that provided by the thiourea alone. Furthermore, the use of the gold–thiourea organocatalyst allows reducing the catalyst loading to 1–3 mol %. This contribution could become an important starting point for further investigations opening a new line of research overlooked so far in the literature.
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spelling pubmed-54850032017-07-11 Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis Izaga, Anabel Herrera, Raquel P. Gimeno, M. Concepción ChemCatChem Full Papers Several group 11 metal complexes with chiral thiourea organocatalysts have been prepared and tested as organocatalysts. The promising results on the influence of metal‐assisted thiourea organocatalysts in the asymmetric Friedel–Crafts alkylation of indole with nitrostyrene are described. Better results with the metal complexes have been achieved because of the cooperative effects between the chiral thiourea and the metal. The synergic effect between both species is higher than the effect promoted by each one separately, especially for gold(I). These outcomes are attributed to a pioneering gold(I) activation of the thiourea catalysts, affording a more acidic and rigid catalytic complex than that provided by the thiourea alone. Furthermore, the use of the gold–thiourea organocatalyst allows reducing the catalyst loading to 1–3 mol %. This contribution could become an important starting point for further investigations opening a new line of research overlooked so far in the literature. John Wiley and Sons Inc. 2017-03-23 2017-04-07 /pmc/articles/PMC5485003/ /pubmed/28706568 http://dx.doi.org/10.1002/cctc.201601527 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Full Papers
Izaga, Anabel
Herrera, Raquel P.
Gimeno, M. Concepción
Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title_full Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title_fullStr Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title_full_unstemmed Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title_short Gold(I)‐Mediated Thiourea Organocatalyst Activation: A Synergic Effect for Asymmetric Catalysis
title_sort gold(i)‐mediated thiourea organocatalyst activation: a synergic effect for asymmetric catalysis
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5485003/
https://www.ncbi.nlm.nih.gov/pubmed/28706568
http://dx.doi.org/10.1002/cctc.201601527
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