Visible Light‐Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three‐Component Photoredox Reaction

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox‐catalyzed three‐component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-07, Vol.25 (38), p.8965-8969
Main Authors: Lipp, Benjamin, Kammer, Lisa Marie, Kücükdisli, Murat, Luque, Adriana, Kühlborn, Jonas, Pusch, Stefan, Matulevičiūtė, Gita, Schollmeyer, Dieter, Šačkus, Algirdas, Opatz, Till
Format: Article
Language:English
Subjects:
arylation
Biomolecules
Chemistry
multicomponent reactions
photoredox catalysis
radical ions
Stereoselectivity
Styrene
Styrenes
sulfonylation
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Summary:Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox‐catalyzed three‐component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene‐functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination. The simultaneous sulfonylation and arylation of styrene derivatives, including complex biomolecules, is achieved in an atom‐economic, operationally simple and scalable three‐component photoredox reaction. It allows for significant structural variation within each component and displays high diastereoselectivity. The reaction operates through a double radical mechanism based on a radical–radical anion coupling.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901175