Visible Light‐Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three‐Component Photoredox Reaction1. Issue 38 (28th May 2019)

• Record Type: Journal Article
• Authors: Lipp, Benjamin; Kammer, Lisa Marie; Kücükdisli, Murat; Luque, Adriana; Kühlborn, Jonas; Pusch, Stefan; Matulevičiūtė, Gita; Schollmeyer, Dieter; Šačkus, Algirdas; Opatz, Till
• Is Part Of: Chemistry. Volume 25:Issue 38(2019)
• Page Start: 8965
• Page End: 8969
• Publication Date: 2019-05-28
• Subjects: arylation -- multicomponent reactions -- photoredox catalysis -- radical ions -- sulfonylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201901175
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : 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.