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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-10419854 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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