Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO
Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine r...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2020
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| _version_ | 1797102551939678208 |
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| author | Davies, TQ Tilby, MJ Skolc, D Hall, A Willis, MC |
| author_facet | Davies, TQ Tilby, MJ Skolc, D Hall, A Willis, MC |
| author_sort | Davies, TQ |
| collection | OXFORD |
| description | Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process. |
| first_indexed | 2024-03-07T06:07:31Z |
| format | Journal article |
| id | oxford-uuid:ee5c2501-a8f0-4de4-8244-e7d16bca8871 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:07:31Z |
| publishDate | 2020 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:ee5c2501-a8f0-4de4-8244-e7d16bca88712022-03-27T11:32:00ZPrimary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSOJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ee5c2501-a8f0-4de4-8244-e7d16bca8871EnglishSymplectic ElementsAmerican Chemical Society2020Davies, TQTilby, MJSkolc, DHall, AWillis, MCSulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process. |
| spellingShingle | Davies, TQ Tilby, MJ Skolc, D Hall, A Willis, MC Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title | Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title_full | Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title_fullStr | Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title_full_unstemmed | Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title_short | Primary sulfonamide synthesis using the sulfinylamine reagent N-sulfinyl-O-(tert-butyl)hydroxylamine, t-BuONSO |
| title_sort | primary sulfonamide synthesis using the sulfinylamine reagent n sulfinyl o tert butyl hydroxylamine t buonso |
| work_keys_str_mv | AT daviestq primarysulfonamidesynthesisusingthesulfinylaminereagentnsulfinylotertbutylhydroxylaminetbuonso AT tilbymj primarysulfonamidesynthesisusingthesulfinylaminereagentnsulfinylotertbutylhydroxylaminetbuonso AT skolcd primarysulfonamidesynthesisusingthesulfinylaminereagentnsulfinylotertbutylhydroxylaminetbuonso AT halla primarysulfonamidesynthesisusingthesulfinylaminereagentnsulfinylotertbutylhydroxylaminetbuonso AT willismc primarysulfonamidesynthesisusingthesulfinylaminereagentnsulfinylotertbutylhydroxylaminetbuonso |