Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate
<p>Sulfonyl chlorides not only play a crucial role in protecting group chemistry but also are important starting materials in the synthesis of sulfonamides, which are in-demand motifs in drug discovery chemistry. Despite their importance, the number of different synthetic approaches to sulfony...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2024
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| _version_ | 1826313795603005440 |
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| author | Pincekova, L Merot, A Schäfer, G Willis, MC |
| author_facet | Pincekova, L Merot, A Schäfer, G Willis, MC |
| author_sort | Pincekova, L |
| collection | OXFORD |
| description | <p>Sulfonyl chlorides not only play a crucial role in protecting group chemistry but also are important starting materials in the synthesis of sulfonamides, which are in-demand motifs in drug discovery chemistry. Despite their importance, the number of different synthetic approaches to sulfonyl chlorides is limited, and most of them rely on traditional oxidative chlorination chemistry from thiol precursors. In this report, we disclose a novel Sandmeyer-type sulfonyl chloride synthesis from feedstock anilines and DABSO, used as a stable SO<sub>2</sub> surrogate, in the presence of HCl and a Cu catalyst. The method works on a wide range of anilines and allows for the isolation of the sulfonyl chloride after aqueous workup or its direct conversion into the sulfonamide by simple addition of an amine after the completion of the Sandmeyer reaction. The scalability of this method was demonstrated on a 20 g scale, and the corresponding heterocyclic sulfonyl chloride was isolated in 80% yield and excellent purity.</p> |
| first_indexed | 2024-09-25T04:20:37Z |
| format | Journal article |
| id | oxford-uuid:796e1709-8045-4671-aeef-45118b57871c |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-09-25T04:20:37Z |
| publishDate | 2024 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:796e1709-8045-4671-aeef-45118b57871c2024-08-07T14:50:20ZSandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogateJournal articlehttp://purl.org/coar/resource_type/c_545buuid:796e1709-8045-4671-aeef-45118b57871cEnglishSymplectic ElementsAmerican Chemical Society2024Pincekova, LMerot, ASchäfer, GWillis, MC<p>Sulfonyl chlorides not only play a crucial role in protecting group chemistry but also are important starting materials in the synthesis of sulfonamides, which are in-demand motifs in drug discovery chemistry. Despite their importance, the number of different synthetic approaches to sulfonyl chlorides is limited, and most of them rely on traditional oxidative chlorination chemistry from thiol precursors. In this report, we disclose a novel Sandmeyer-type sulfonyl chloride synthesis from feedstock anilines and DABSO, used as a stable SO<sub>2</sub> surrogate, in the presence of HCl and a Cu catalyst. The method works on a wide range of anilines and allows for the isolation of the sulfonyl chloride after aqueous workup or its direct conversion into the sulfonamide by simple addition of an amine after the completion of the Sandmeyer reaction. The scalability of this method was demonstrated on a 20 g scale, and the corresponding heterocyclic sulfonyl chloride was isolated in 80% yield and excellent purity.</p> |
| spellingShingle | Pincekova, L Merot, A Schäfer, G Willis, MC Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title | Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title_full | Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title_fullStr | Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title_full_unstemmed | Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title_short | Sandmeyer chlorosulfonylation of (hetero)aromatic amines using DABSO as an SO2 surrogate |
| title_sort | sandmeyer chlorosulfonylation of hetero aromatic amines using dabso as an so2 surrogate |
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