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Thesis

Organocatalytic Oxidative Couplings: From Mechanistic Studies to New Radical Reactions

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Schweitzer-Chaput,  Bertrand
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Schweitzer-Chaput, B. (2014). Organocatalytic Oxidative Couplings: From Mechanistic Studies to New Radical Reactions. PhD Thesis, Universität zu Köln, Köln.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-BAC1-7
Abstract
The use of peroxides as intermediates in oxidative coupling chemistry is presented in this PhD work. A one pot protocol for a metal-free C-H functionalization of protected tetrahydroisoquinolines, proceeding via acid catalysed substitution of a peroxide moiety was developed. Mechanistic studies on the autoxidative coupling reaction of xanthene and ketones were performed and a novel mode of activation of simple ketones in the presence of a hydroperoxide and a strong acid was identified. Rationalisation of this phenomenon was achieved via the involvement of alkenyl peroxides as crucial intermediates. α-Carbonyl radicals are generated in this process and their synthetic utility was evaluated. In particular, a multicomponent oxidative radical addition of ketones and hydroperoxides to olefins, affording valuable ϒ-peroxyketones, was developed.