One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate w...
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| Format: | Journal article |
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Royal Society of Chemistry
2016
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| _version_ | 1826282576004775936 |
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| author | Davies, A Curto, J Bagley, S Willis, M |
| author_facet | Davies, A Curto, J Bagley, S Willis, M |
| author_sort | Davies, A |
| collection | OXFORD |
| description | A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation succesfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated. |
| first_indexed | 2024-03-07T00:45:56Z |
| format | Journal article |
| id | oxford-uuid:84a8c85d-2e17-4e3b-9617-f28b863d31dc |
| institution | University of Oxford |
| last_indexed | 2024-03-07T00:45:56Z |
| publishDate | 2016 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:84a8c85d-2e17-4e3b-9617-f28b863d31dc2022-03-26T21:52:30ZOne-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:84a8c85d-2e17-4e3b-9617-f28b863d31dcSymplectic Elements at OxfordRoyal Society of Chemistry2016Davies, ACurto, JBagley, SWillis, MA mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation succesfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated. |
| spellingShingle | Davies, A Curto, J Bagley, S Willis, M One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title | One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title_full | One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title_fullStr | One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title_full_unstemmed | One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title_short | One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| title_sort | one pot palladium catalyzed synthesis of sulfonyl fluorides from aryl bromides |
| work_keys_str_mv | AT daviesa onepotpalladiumcatalyzedsynthesisofsulfonylfluoridesfromarylbromides AT curtoj onepotpalladiumcatalyzedsynthesisofsulfonylfluoridesfromarylbromides AT bagleys onepotpalladiumcatalyzedsynthesisofsulfonylfluoridesfromarylbromides AT willism onepotpalladiumcatalyzedsynthesisofsulfonylfluoridesfromarylbromides |