Visible Light-Driven, Persulfate-Mediated Hydrocarboxylation of Vinylsulfones

We report a visible light-mediated approach for the radical hydrocarboxylation of vinylsulfone derivatives. Using cheap and easily accessible sodium formate as C1-source and K2S2O8 as reagent, a set of vinylsulfone substrates could be efficiently hydrocarboxylated in aqueous medium without any addit...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 365; no. 18; pp. 3069 - 3074
Main Authors Palvoelgyi, Adam Mark, Scharinger, Fabian, Bauhoff, Thomas, Bica-Schroeder, Katharina
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.09.2023
Wiley Subscription Services, Inc
Subjects
Aqueous solutions
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Potassium persulfate
Reagents
Science & Technology
Substrates
STYRENES
CO2 radical anion
CATALYZED HYDROCARBOXYLATION
ACTIVATION
Hydrocarboxylation
FORMATE
CO2
PHOTOCATALYSIS
COMPLEXES
Visible light
Potassium persulfate
BETA-SELECTIVE HYDROCARBOXYLATION
Hydrogen atom transfer
HYDROXYCARBONYLATION
C-H
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Summary:We report a visible light-mediated approach for the radical hydrocarboxylation of vinylsulfone derivatives. Using cheap and easily accessible sodium formate as C1-source and K2S2O8 as reagent, a set of vinylsulfone substrates could be efficiently hydrocarboxylated in aqueous medium without any additional catalyst or reagent; and the concept could be also applied for direct hydroacylations, hydroalkylations and hydrophosphorylations. The control experiments clearly indicated that the reaction proceeds via radical mechanism without the generation of electron donor-acceptor (EDA) complexes; supporting the working model of K2S2O8-initiated in situ formation of CO2 radical anion.
Bibliography:European Research Council (ERC)
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300654