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DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups

Organic thioethers play an important role in the discovery of drugs and natural products. However, the green synthesis of organic sulfide compounds remains a challenging task. The convenient and efficient synthesis of 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via the mediat...

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Autores principales: Zhou, Yong-Jun, Fang, Yong-Gan, Yang, Kai, Lin, Jian-Yun, Li, Huan-Qing, Chen, Zu-Jia, Wang, Zhao-Yang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10419854/
https://www.ncbi.nlm.nih.gov/pubmed/37570605
http://dx.doi.org/10.3390/molecules28155635
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author Zhou, Yong-Jun
Fang, Yong-Gan
Yang, Kai
Lin, Jian-Yun
Li, Huan-Qing
Chen, Zu-Jia
Wang, Zhao-Yang
author_facet Zhou, Yong-Jun
Fang, Yong-Gan
Yang, Kai
Lin, Jian-Yun
Li, Huan-Qing
Chen, Zu-Jia
Wang, Zhao-Yang
author_sort Zhou, Yong-Jun
collection PubMed
description Organic thioethers play an important role in the discovery of drugs and natural products. However, the green synthesis of organic sulfide compounds remains a challenging task. The convenient and efficient synthesis of 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via the mediation of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), affording a facile route for the sulfur-functionalization of 3,4-dihalo-2(5H)-furanones under transition metal-free conditions. This new approach has demonstrated the functionalization of non-aromatic C(sp2)-X-type halides with unique structures containing C-X, C-O, C=O and C=C bonds. Compared with traditional synthesis methods using transition metal catalysts with ligands, this reaction has many advantages, such as the lower temperature, the shorter reaction time, the wide substrate range and good functional group tolerance. Notably, DMSO plays multiple roles, and is simultaneously used as an odorless methylthiolating reagent and safe solvent.
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spelling pubmed-104198542023-08-12 DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups Zhou, Yong-Jun Fang, Yong-Gan Yang, Kai Lin, Jian-Yun Li, Huan-Qing Chen, Zu-Jia Wang, Zhao-Yang Molecules Article Organic thioethers play an important role in the discovery of drugs and natural products. However, the green synthesis of organic sulfide compounds remains a challenging task. The convenient and efficient synthesis of 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via the mediation of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), affording a facile route for the sulfur-functionalization of 3,4-dihalo-2(5H)-furanones under transition metal-free conditions. This new approach has demonstrated the functionalization of non-aromatic C(sp2)-X-type halides with unique structures containing C-X, C-O, C=O and C=C bonds. Compared with traditional synthesis methods using transition metal catalysts with ligands, this reaction has many advantages, such as the lower temperature, the shorter reaction time, the wide substrate range and good functional group tolerance. Notably, DMSO plays multiple roles, and is simultaneously used as an odorless methylthiolating reagent and safe solvent. MDPI 2023-07-25 /pmc/articles/PMC10419854/ /pubmed/37570605 http://dx.doi.org/10.3390/molecules28155635 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 Article
Zhou, Yong-Jun
Fang, Yong-Gan
Yang, Kai
Lin, Jian-Yun
Li, Huan-Qing
Chen, Zu-Jia
Wang, Zhao-Yang
DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title_full DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title_fullStr DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title_full_unstemmed DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title_short DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
title_sort dbdmh-promoted methylthiolation in dmso: a metal-free protocol to methyl sulfur compounds with multifunctional groups
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10419854/
https://www.ncbi.nlm.nih.gov/pubmed/37570605
http://dx.doi.org/10.3390/molecules28155635
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