Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation
Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed hydrosulfonylation...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2020
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| _version_ | 1797059390586486784 |
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| author | Hell, SM Meyer, CF Misale, A Sap, JBI Christensen, KE Willis, MC Trabanco, AA Gouverneur, V |
| author_facet | Hell, SM Meyer, CF Misale, A Sap, JBI Christensen, KE Willis, MC Trabanco, AA Gouverneur, V |
| author_sort | Hell, SM |
| collection | OXFORD |
| description | Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed hydrosulfonylation of electron‐deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity‐reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This late‐stage functionalization method tolerates a remarkably wide range of functional groups, is operationally simple, scalable, and allows access to building blocks which are important for medicinal chemistry and drug discovery. |
| first_indexed | 2024-03-06T20:03:33Z |
| format | Journal article |
| id | oxford-uuid:2829247c-d11b-4315-ad46-cb7443e601f1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T20:03:33Z |
| publishDate | 2020 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:2829247c-d11b-4315-ad46-cb7443e601f12022-03-26T12:11:10ZHydrosulfonylation of alkenes with sulfonyl chlorides under visible light activationJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2829247c-d11b-4315-ad46-cb7443e601f1EnglishSymplectic ElementsWiley2020Hell, SMMeyer, CFMisale, ASap, JBIChristensen, KEWillis, MCTrabanco, AAGouverneur, VSulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox‐catalyzed hydrosulfonylation of electron‐deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity‐reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This late‐stage functionalization method tolerates a remarkably wide range of functional groups, is operationally simple, scalable, and allows access to building blocks which are important for medicinal chemistry and drug discovery. |
| spellingShingle | Hell, SM Meyer, CF Misale, A Sap, JBI Christensen, KE Willis, MC Trabanco, AA Gouverneur, V Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title | Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title_full | Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title_fullStr | Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title_full_unstemmed | Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title_short | Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
| title_sort | hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation |
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