Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium
Abstract Sulfur-containing units are fundamental components widely found in bioactive compounds, prompting notable efforts toward developing synthetic methodologies for incorporating sulfur functionality into organic precursors. The synthesis of sulfinate esters and sulfinamides has garnered signifi...
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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/s41467-024-55786-7 |
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| author | Yifan Li Weigang Zhang Jeonguk Kweon Yi Pan Qing Wang Sukbok Chang Yi Wang |
| author_facet | Yifan Li Weigang Zhang Jeonguk Kweon Yi Pan Qing Wang Sukbok Chang Yi Wang |
| author_sort | Yifan Li |
| collection | DOAJ |
| description | Abstract Sulfur-containing units are fundamental components widely found in bioactive compounds, prompting notable efforts toward developing synthetic methodologies for incorporating sulfur functionality into organic precursors. The synthesis of sulfinate esters and sulfinamides has garnered significant interest owing to their immense potential for applications, especially in drug development. However, most existing synthetic protocols suffer from some limitations. To address these challenges, we herein present a practical and efficient approach for the reductive sulfinylation of diverse nucleophiles with sulfonylpyridinium salts (SulPy) through the nucleophilic chain substitution, namely SNC reaction, which involves S(VI) to S(IV) nucleophilic chain isomerization process. These versatile sulfinylation reagents can be readily accessed from diverse commercially available resourses. The late-stage modification of complex molecules and the ability to rapidly synthesize numerous sulfinyl bioisosteres of various drugs highlights the utility of this protocol. |
| format | Article |
| id | doaj-art-3a411cf8821741d79d7e29c30b37c18b |
| institution | DOAJ |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-3a411cf8821741d79d7e29c30b37c18b2025-08-20T02:53:57ZengNature PortfolioNature Communications2041-17232025-01-0116111210.1038/s41467-024-55786-7Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridiniumYifan Li0Weigang Zhang1Jeonguk Kweon2Yi Pan3Qing Wang4Sukbok Chang5Yi Wang6Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing UniversityJiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing UniversityCenter for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing UniversityCenter for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing UniversityAbstract Sulfur-containing units are fundamental components widely found in bioactive compounds, prompting notable efforts toward developing synthetic methodologies for incorporating sulfur functionality into organic precursors. The synthesis of sulfinate esters and sulfinamides has garnered significant interest owing to their immense potential for applications, especially in drug development. However, most existing synthetic protocols suffer from some limitations. To address these challenges, we herein present a practical and efficient approach for the reductive sulfinylation of diverse nucleophiles with sulfonylpyridinium salts (SulPy) through the nucleophilic chain substitution, namely SNC reaction, which involves S(VI) to S(IV) nucleophilic chain isomerization process. These versatile sulfinylation reagents can be readily accessed from diverse commercially available resourses. The late-stage modification of complex molecules and the ability to rapidly synthesize numerous sulfinyl bioisosteres of various drugs highlights the utility of this protocol.https://doi.org/10.1038/s41467-024-55786-7 |
| spellingShingle | Yifan Li Weigang Zhang Jeonguk Kweon Yi Pan Qing Wang Sukbok Chang Yi Wang Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium Nature Communications |
| title | Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| title_full | Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| title_fullStr | Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| title_full_unstemmed | Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| title_short | Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| title_sort | reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium |
| url | https://doi.org/10.1038/s41467-024-55786-7 |
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