Mechanistic Study of the Titanocene(III)-Catalyzed Radical Arylation of Epoxides

TitleMechanistic Study of the Titanocene(III)-Catalyzed Radical Arylation of Epoxides
Publication TypeJournal Article
Year of Publication2015
AuthorsGansauer A, von Laufenberg D, Kube C, Dahmen T, Michelmann A, Behlendorf M, Sure R, Seddiqzai M, Grimme S, Sadasivam DV, Fianu G, Flowers, II RA
JournalChemistry - A European Journal
Volume21
Issue1
Start Page280
Pagination280-288
Date Published01/2015
Abstract

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.

URLhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201404404/abstract
DOI10.1002/chem.201404404