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Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts

An efficient synthesis of methoxy-substituted thioxanthylium salts has been developed. The reaction of diaryl sulfides with benzoyl chlorides in the presence of TfOH smoothly proceeded to give the desired thioxanthylium salts in good yields. In their UV–vis spectra, the maximum absorption wavelength...

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Autores principales: Tanaka, Kenta, Tanaka, Yuta, Kishimoto, Mami, Hoshino, Yujiro, Honda, Kiyoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6753671/
https://www.ncbi.nlm.nih.gov/pubmed/31579074
http://dx.doi.org/10.3762/bjoc.15.208
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author Tanaka, Kenta
Tanaka, Yuta
Kishimoto, Mami
Hoshino, Yujiro
Honda, Kiyoshi
author_facet Tanaka, Kenta
Tanaka, Yuta
Kishimoto, Mami
Hoshino, Yujiro
Honda, Kiyoshi
author_sort Tanaka, Kenta
collection PubMed
description An efficient synthesis of methoxy-substituted thioxanthylium salts has been developed. The reaction of diaryl sulfides with benzoyl chlorides in the presence of TfOH smoothly proceeded to give the desired thioxanthylium salts in good yields. In their UV–vis spectra, the maximum absorption wavelengths of methoxy-functionalized thioxanthylium salts were observed at around 460 nm, which show a drastic red shift compared to the parent thioxanthylium salts. The present reaction provides a versatile access to functionalized thioxanthylium salts, and therefore it constitutes a promising tool for the synthesis of biologically and photochemically active molecules.
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spelling pubmed-67536712019-10-02 Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts Tanaka, Kenta Tanaka, Yuta Kishimoto, Mami Hoshino, Yujiro Honda, Kiyoshi Beilstein J Org Chem Full Research Paper An efficient synthesis of methoxy-substituted thioxanthylium salts has been developed. The reaction of diaryl sulfides with benzoyl chlorides in the presence of TfOH smoothly proceeded to give the desired thioxanthylium salts in good yields. In their UV–vis spectra, the maximum absorption wavelengths of methoxy-functionalized thioxanthylium salts were observed at around 460 nm, which show a drastic red shift compared to the parent thioxanthylium salts. The present reaction provides a versatile access to functionalized thioxanthylium salts, and therefore it constitutes a promising tool for the synthesis of biologically and photochemically active molecules. Beilstein-Institut 2019-09-05 /pmc/articles/PMC6753671/ /pubmed/31579074 http://dx.doi.org/10.3762/bjoc.15.208 Text en Copyright © 2019, Tanaka et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tanaka, Kenta
Tanaka, Yuta
Kishimoto, Mami
Hoshino, Yujiro
Honda, Kiyoshi
Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title_full Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title_fullStr Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title_full_unstemmed Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title_short Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
title_sort friedel–crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6753671/
https://www.ncbi.nlm.nih.gov/pubmed/31579074
http://dx.doi.org/10.3762/bjoc.15.208
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