Rapid and scalable halosulfonylation of strain-release reagents
<p>Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug and agrochemical candidates, are limited. Here we report a solutio...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2022
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| _version_ | 1826316104161558528 |
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| author | Pickford, HD Ripenko, V McNamee, RE Holovchuk, S Thompson, AL Smith, RC Mykhailiuk, PK Anderson, EA |
| author_facet | Pickford, HD Ripenko, V McNamee, RE Holovchuk, S Thompson, AL Smith, RC Mykhailiuk, PK Anderson, EA |
| author_sort | Pickford, HD |
| collection | OXFORD |
| description | <p>Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug and agrochemical candidates, are limited. Here we report a solution to this challenge: a one-pot halosulfonylation of [1.1.1]propellane, [3.1.1]propellane and bicyclo[1.1.0]butanes that proceeds under practical, scalable and mild conditions. The sulfonyl halides used in this chemistry feature aryl, heteroaryl and alkyl substituents, and are conveniently generated in situ from readily available sulfinate salts and halogen atom sources. This methodology enables the synthesis of an array of pharmaceutically and agrochemically relevant halogen/sulfonyl-substituted bioisosteres and cyclobutanes, on up to multidecagram scale.</p> |
| first_indexed | 2024-03-07T07:36:57Z |
| format | Journal article |
| id | oxford-uuid:c5929347-5803-48fa-a727-b5543748d056 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-12-09T03:37:43Z |
| publishDate | 2022 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:c5929347-5803-48fa-a727-b5543748d0562024-12-02T14:42:58ZRapid and scalable halosulfonylation of strain-release reagentsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c5929347-5803-48fa-a727-b5543748d056EnglishSymplectic ElementsWiley2022Pickford, HDRipenko, VMcNamee, REHolovchuk, SThompson, ALSmith, RCMykhailiuk, PKAnderson, EA<p>Sulfonylated aromatics are commonplace motifs in drugs and agrochemicals. However, methods for the direct synthesis of sulfonylated non-classical arene bioisosteres, which could improve the physicochemical properties of drug and agrochemical candidates, are limited. Here we report a solution to this challenge: a one-pot halosulfonylation of [1.1.1]propellane, [3.1.1]propellane and bicyclo[1.1.0]butanes that proceeds under practical, scalable and mild conditions. The sulfonyl halides used in this chemistry feature aryl, heteroaryl and alkyl substituents, and are conveniently generated in situ from readily available sulfinate salts and halogen atom sources. This methodology enables the synthesis of an array of pharmaceutically and agrochemically relevant halogen/sulfonyl-substituted bioisosteres and cyclobutanes, on up to multidecagram scale.</p> |
| spellingShingle | Pickford, HD Ripenko, V McNamee, RE Holovchuk, S Thompson, AL Smith, RC Mykhailiuk, PK Anderson, EA Rapid and scalable halosulfonylation of strain-release reagents |
| title | Rapid and scalable halosulfonylation of strain-release reagents |
| title_full | Rapid and scalable halosulfonylation of strain-release reagents |
| title_fullStr | Rapid and scalable halosulfonylation of strain-release reagents |
| title_full_unstemmed | Rapid and scalable halosulfonylation of strain-release reagents |
| title_short | Rapid and scalable halosulfonylation of strain-release reagents |
| title_sort | rapid and scalable halosulfonylation of strain release reagents |
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