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Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation
Author(s) -
Rohe Samantha,
Morris Avery O.,
McCallum Terry,
Barriault Louis
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810187
Subject(s) - chemistry , oxidizing agent , catalysis , photochemistry , chlorine , redox , hydrogen atom , photoredox catalysis , chloride , inert , atom (system on chip) , surface modification , hydrogen , inorganic chemistry , organic chemistry , photocatalysis , group (periodic table) , computer science , embedded system
The selective functionalization of chemically inert C−H bonds remains to be fully realized in achieving organic transformations that are redox‐neutral, waste‐limiting, and atom‐economical. The catalytic generation of chlorine atoms from chloride ions is one of the most challenging redox processes, where the requirement of harsh and oxidizing reaction conditions renders it seldom utilized in synthetic applications. We report the mild, controlled, and catalytic generation of chlorine atoms as a new opportunity for access to a wide variety of hydrogen atom transfer (HAT) reactions owing to the high stability of HCl. The discovery of the photoredox mediated generation of chlorine atoms with Ir‐based polypyridyl complex, [Ir(dF(CF 3 )ppy) 2 (dtbbpy)]Cl, under blue LED irradiation is reported.