Generation of perthiyl radicals for the synthesis of unsymmetric disulfides
Abstract Unsymmetric disulfides are prevalent in natural products and are essential in medicinal chemistry and materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric disulfides...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55310-x |
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| author | Fei Zhou Xiaochun He Mi Zhou Na Li Qingqing Wang Xuemei Zhang Zhong Lian |
| author_facet | Fei Zhou Xiaochun He Mi Zhou Na Li Qingqing Wang Xuemei Zhang Zhong Lian |
| author_sort | Fei Zhou |
| collection | DOAJ |
| description | Abstract Unsymmetric disulfides are prevalent in natural products and are essential in medicinal chemistry and materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric disulfides through the addition of perthiyl radicals to alkenes. This study marks the use of generating perthiyl radicals by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary and tertiary alkyl (pseudo)halides substituted with different functional groups successfully function as suitable reactants. The formation of perthiyl radicals and their involvement in the reaction process are verified through mechanistic studies and DFT calculations. Overall, this method leverages readily available alkyl electrophiles and alkenes alongside SO2 in a single reaction setup to efficiently form both carbon-sulfur and sulfur-sulfur bonds simultaneously. |
| format | Article |
| id | doaj-art-72d86c2393c14f79ab1b517cb1b5262e |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-72d86c2393c14f79ab1b517cb1b5262e2025-01-05T12:38:34ZengNature PortfolioNature Communications2041-17232025-01-0116111010.1038/s41467-024-55310-xGeneration of perthiyl radicals for the synthesis of unsymmetric disulfidesFei Zhou0Xiaochun He1Mi Zhou2Na Li3Qingqing Wang4Xuemei Zhang5Zhong Lian6Department of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityDepartment of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityDepartment of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityWarshel Institute for Computational Biology, School of Medicine, The Chinese University of Hong KongDepartment of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityDepartment of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityDepartment of Dermatology, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan UniversityAbstract Unsymmetric disulfides are prevalent in natural products and are essential in medicinal chemistry and materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric disulfides through the addition of perthiyl radicals to alkenes. This study marks the use of generating perthiyl radicals by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary and tertiary alkyl (pseudo)halides substituted with different functional groups successfully function as suitable reactants. The formation of perthiyl radicals and their involvement in the reaction process are verified through mechanistic studies and DFT calculations. Overall, this method leverages readily available alkyl electrophiles and alkenes alongside SO2 in a single reaction setup to efficiently form both carbon-sulfur and sulfur-sulfur bonds simultaneously.https://doi.org/10.1038/s41467-024-55310-x |
| spellingShingle | Fei Zhou Xiaochun He Mi Zhou Na Li Qingqing Wang Xuemei Zhang Zhong Lian Generation of perthiyl radicals for the synthesis of unsymmetric disulfides Nature Communications |
| title | Generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| title_full | Generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| title_fullStr | Generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| title_full_unstemmed | Generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| title_short | Generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| title_sort | generation of perthiyl radicals for the synthesis of unsymmetric disulfides |
| url | https://doi.org/10.1038/s41467-024-55310-x |
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