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Activation and C−C Coupling of Aryl Iodides via Bismuth Photocatalysis

Mauro Mato, Alexios Stamoulis, Paolo Cleto Bruzzese, Josep Cornellà

2024Angewandte Chemie International Edition33 citationsDOIOpen Access PDF

Abstract

Abstract Within the emerging field of bismuth redox catalysis, the catalytic formation of C−C bonds using aryl halides would be highly desirable; yet such a process remains a synthetic challenge. Herein, we present a chemoselective bismuth‐photocatalyzed activation and subsequent coupling of (hetero)aryl iodides with pyrrole derivatives to access C(sp 2 )−C(sp 2 ) linkages through C−H functionalization. This unique reactivity is the result of the bismuth complex featuring two redox state‐dependent interactions with light, which 1) activates the Bi(I) complex for oxidative addition via MLCT, and 2) promotes the homolytic cleavage of aryl Bi(III) intermediates through a LLCT process.

Topics & Concepts

ArylBismuthChemistryCatalysisHomolysisPhotocatalysisHalideRedoxPhotochemistryBond cleavageAryl halideCombinatorial chemistryReactivity (psychology)Organic chemistryRadicalMedicinePathologyAlkylAlternative medicineRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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