Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

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Abstract: 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation ; volume:132 ; number:28 ; year:2020 ; pages:11717-11723 ; extent:7
Angewandte Chemie ; 132, Heft 28 (2020), 11717-11723 (gesamt 7)

Creator: Hell, Sandrine M.
Meyer, Claudio F.
Misale, Antonio
Sap, Jeroen B. I.
Christensen, Kirsten E.
Willis, Michael C.
Trabanco, Andrés A.
Gouverneur, Véronique

DOI: 10.1002/ange.202004070

URN: urn:nbn:de:101:1-2022052811163090577182

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:20 AM CEST

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Associated

Hell, Sandrine M.
Meyer, Claudio F.
Misale, Antonio
Sap, Jeroen B. I.
Christensen, Kirsten E.
Willis, Michael C.
Trabanco, Andrés A.
Gouverneur, Véronique

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Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters

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Visible light-induced chemoselective 1,2-diheteroarylation of alkenes

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Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

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Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis

Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis

Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis

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Oxidative reaction of 2-aminopyridine-3-sulfonyl chlorides with tertiary amines

Oxidative reaction of 2-aminopyridine-3-sulfonyl chlorides with tertiary amines

A Novel, Practical Synthesis of Sulfonyl Chlorides from Thiol and Disulfide Derivatives

A Novel, Practical Synthesis of Sulfonyl Chlorides from Thiol and Disulfide Derivatives

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters

Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

Three‐Component Radical Cross‐Coupling: Asymmetric Vicinal Sulfonyl‐Esterification of Alkenes Involving Sulfur Dioxide

Visible light-mediated difluoroalkylation of electron-deficient alkenes

Visible light-mediated difluoroalkylation of electron-deficient alkenes

Visible light-induced chemoselective 1,2-diheteroarylation of alkenes

Visible light-induced chemoselective 1,2-diheteroarylation of alkenes

Sulfonylative and Azidosulfonylative Cyclizations by Visible‐Light‐Photosensitization of Sulfonyl Azides in THF

Sulfonylative and Azidosulfonylative Cyclizations by Visible‐Light‐Photosensitization of Sulfonyl Azides in THF

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