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Nickel Meets Aryl Thianthrenium Salts: Ni(I)-Catalyzed Halogenation of Arenes

Shengyang Ni, Jiyao Yan, Srija Tewari, Edward J. Reijerse, Tobias Ritter, Josep Cornellà

2023Journal of the American Chemical Society105 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide Herein, a regioselective, late-stage two-step arene halogenation method is reported. We propose how unusual Ni(I)/(III) catalysis is enabled by a combination of aryl thianthrenium and Ni redox properties that is hitherto unachieved with other (pseudo)halides. The catalyst is accessed in situ from inexpensive NiCl 2 ·6(H 2 O) and zinc without the need of supporting ligands.

Topics & Concepts

ChemistryHalogenationRegioselectivityCatalysisArylHalideNickelRedoxZincOrganic chemistryCombinatorial chemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques