Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives

A novel double Friedel–Crafts reaction of acylsilanes in water is described. This strategy enables synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. Compared to the 1-silyl-bis(indolyl)methane derivatives from indole substrate, 1-hydroxy-b...

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Detalles Bibliográficos
Autores principales: Li, Qi, Liang, Xiu-Xia, Zhang, Wang, Han, Man-Yi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420641/
https://www.ncbi.nlm.nih.gov/pubmed/37570655
http://dx.doi.org/10.3390/molecules28155685
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author Li, Qi
Liang, Xiu-Xia
Zhang, Wang
Han, Man-Yi
author_facet Li, Qi
Liang, Xiu-Xia
Zhang, Wang
Han, Man-Yi
author_sort Li, Qi
collection PubMed
description A novel double Friedel–Crafts reaction of acylsilanes in water is described. This strategy enables synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. Compared to the 1-silyl-bis(indolyl)methane derivatives from indole substrate, 1-hydroxy-bis(indolyl)methane derivatives were synthesized from the 5-hydroxyindole, and the hydrogen bonds in the 5-hydroxyindole play a crucial role in regulating the reaction selectivity.
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spelling pubmed-104206412023-08-12 Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives Li, Qi Liang, Xiu-Xia Zhang, Wang Han, Man-Yi Molecules Communication A novel double Friedel–Crafts reaction of acylsilanes in water is described. This strategy enables synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. Compared to the 1-silyl-bis(indolyl)methane derivatives from indole substrate, 1-hydroxy-bis(indolyl)methane derivatives were synthesized from the 5-hydroxyindole, and the hydrogen bonds in the 5-hydroxyindole play a crucial role in regulating the reaction selectivity. MDPI 2023-07-27 /pmc/articles/PMC10420641/ /pubmed/37570655 http://dx.doi.org/10.3390/molecules28155685 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Li, Qi
Liang, Xiu-Xia
Zhang, Wang
Han, Man-Yi
Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title_full Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title_fullStr Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title_full_unstemmed Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title_short Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
title_sort friedel–crafts reaction of acylsilanes: highly chemoselective synthesis of 1-hydroxy-bis(indolyl)methanes and 1-silyl-bis(indolyl)methanes derivatives
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420641/
https://www.ncbi.nlm.nih.gov/pubmed/37570655
http://dx.doi.org/10.3390/molecules28155685
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