Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation
We report a route to benzosultams that exploits the palladium-catalysed aminsulfonylation of alkenyl iodides as the initial step. An (Z)-configured alkenyl iodide substrate is combined with DABSO, a N,N-dialkylhydrazine nucleophile and a palladium(0) catalyst to achieve aminsulfonylation. A second p...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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Elsevier
2021
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| _version_ | 1826298984707129344 |
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| author | Richards-Taylor, C Willis, M |
| author_facet | Richards-Taylor, C Willis, M |
| author_sort | Richards-Taylor, C |
| collection | OXFORD |
| description | We report a route to benzosultams that exploits the palladium-catalysed aminsulfonylation of alkenyl iodides as the initial step. An (Z)-configured alkenyl iodide substrate is combined with DABSO, a N,N-dialkylhydrazine nucleophile and a palladium(0) catalyst to achieve aminsulfonylation. A second palladium(0)-catalysed transformation, this time intramolecular, leads to benzosultam formation. Good variation of the starting alkenyl iodides is possible. A related SNAr route was also explored, but was shown to be less efficient. |
| first_indexed | 2024-03-07T04:55:01Z |
| format | Journal article |
| id | oxford-uuid:d64c2333-d11c-4a57-8575-7a2774f4df26 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:55:01Z |
| publishDate | 2021 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:d64c2333-d11c-4a57-8575-7a2774f4df262022-03-27T08:32:35ZBenzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidationJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d64c2333-d11c-4a57-8575-7a2774f4df26EnglishSymplectic ElementsElsevier2021Richards-Taylor, CWillis, MWe report a route to benzosultams that exploits the palladium-catalysed aminsulfonylation of alkenyl iodides as the initial step. An (Z)-configured alkenyl iodide substrate is combined with DABSO, a N,N-dialkylhydrazine nucleophile and a palladium(0) catalyst to achieve aminsulfonylation. A second palladium(0)-catalysed transformation, this time intramolecular, leads to benzosultam formation. Good variation of the starting alkenyl iodides is possible. A related SNAr route was also explored, but was shown to be less efficient. |
| spellingShingle | Richards-Taylor, C Willis, M Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title | Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title_full | Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title_fullStr | Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title_full_unstemmed | Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title_short | Benzosultam synthesis exploiting sequential palladium-catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
| title_sort | benzosultam synthesis exploiting sequential palladium catalysed intermolecular aminosulfonylation and intramolecular sulfamidation |
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