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Mechanistic Study of the Titanocene(III)‐Catalyzed Radical Arylation of Epoxides
Author(s) -
Gansäuer Andreas,
von Laufenberg Daniel,
Kube Christian,
Dahmen Tobias,
Michelmann Antonius,
Behlendorf Maike,
Sure Rebecca,
Seddiqzai Meriam,
Grimme Stefan,
Sadasivam Dhandapani V.,
Fianu Godfred D.,
Flowers II Robert A.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404404
Subject(s) - catalysis , epoxide , radical , chemistry , proton , reactive intermediate , electron transfer , combinatorial chemistry , photochemistry , computational chemistry , organic chemistry , physics , quantum mechanics
An atom‐economical and catalytic arylation of epoxide‐derived radicals is described. The key step of the catalytic system is a sequential electron and proton transfer for the rearomatization of the radical σ‐complex and catalyst regeneration. Kinetic, computational, spectroscopic, and cyclovoltammetric investigations highlight the key issues of the reaction mechanism and catalyst stabilization by collidine hydrochloride. Studies employing radicophiles rule out the participation of cations as reactive intermediates.