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Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes


Du, Xiaoyong; Cheng-Sánchez, Iván; Nevado, Cristina (2023). Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes. Journal of the American Chemical Society, 145(23):12532-12540.

Abstract

An asymmetricthree-componentcarbosulfonylationof alkenesis presentedhere. The reaction,involvingthesimultaneousformationof a C−C and a C−S bond acrosstheπ-system,uses a dual nickel/photoredoxcatalyticsystemto producebothβ-aryl andβ-alkenylsulfonesin high yields and with excellentlevels of stereocontrol(up to 99:1 er). This protocolexhibitsabroadsubstratescope and excellentfunctionalgrouptoleranceand its syntheticpotentialhas been demonstratedby successfulapplicationstowardpharmacologicallyrelevantmolecules.A broadarray of controlexperimentssupportsthe involvementof asecondaryalkyl radicalintermediategeneratedthroughradicaladditionof a sulfonylradicalto the doublebond.Moreover,stoichiometricand cross-overexperimentsfurthersuggestan underlyingNi(0)/Ni(I)/Ni(III)pathwayoperativein thesetransformations.

Abstract

An asymmetricthree-componentcarbosulfonylationof alkenesis presentedhere. The reaction,involvingthesimultaneousformationof a C−C and a C−S bond acrosstheπ-system,uses a dual nickel/photoredoxcatalyticsystemto producebothβ-aryl andβ-alkenylsulfonesin high yields and with excellentlevels of stereocontrol(up to 99:1 er). This protocolexhibitsabroadsubstratescope and excellentfunctionalgrouptoleranceand its syntheticpotentialhas been demonstratedby successfulapplicationstowardpharmacologicallyrelevantmolecules.A broadarray of controlexperimentssupportsthe involvementof asecondaryalkyl radicalintermediategeneratedthroughradicaladditionof a sulfonylradicalto the doublebond.Moreover,stoichiometricand cross-overexperimentsfurthersuggestan underlyingNi(0)/Ni(I)/Ni(III)pathwayoperativein thesetransformations.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Life Sciences > Biochemistry
Physical Sciences > Colloid and Surface Chemistry
Uncontrolled Keywords:Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
Language:English
Date:30 May 2023
Deposited On:19 Feb 2024 14:59
Last Modified:30 Jun 2024 01:37
Publisher:American Chemical Society (ACS)
ISSN:0002-7863
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1021/jacs.3c00744
PubMed ID:37249908
Project Information:
  • : FunderSNF
  • : Grant ID200021_184986/1
  • : Project Title
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)