Development of New Radical Cascades and Multi-Component Reactions
Application to the Synthesis of Nitrogen-Containing Heterocycles
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In this dissertation Marie-Hélène Larraufie develops original radical and pallado-catalyzed methodologies making it possible to synthesise several classes of bioactive nitrogen-containing heterocycles. New radical cascades employing the N-acylcyanamide moiety offer straightforward routes to quinazolinones and guanidines, as well as new insights into the mechanism of homolytic aromatic substitutions. In parallel, the scope of visible light photoredox catalysis is expanded to the ring opening of epoxides and aziridines, thus providing new sustainable alternatives for the generation of radicals...
In this dissertation Marie-Hélène Larraufie develops original radical and pallado-catalyzed methodologies making it possible to synthesise several classes of bioactive nitrogen-containing heterocycles. New radical cascades employing the N-acylcyanamide moiety offer straightforward routes to quinazolinones and guanidines, as well as new insights into the mechanism of homolytic aromatic substitutions. In parallel, the scope of visible light photoredox catalysis is expanded to the ring opening of epoxides and aziridines, thus providing new sustainable alternatives for the generation of radicals. Further, in a collaborative effort with the Catellani group, the author investigated dual palladium/norbornene catalysis. First, a C-amination coupling variant of the Catellani reaction with unprotected amines is developed, providing an expeditious route to phenanthridines. Then, the influence of the chelating effect on Pd(IV) intermediates reactivity is examined with the help of experimental studies and DFT calculations. The work in this thesis has resulted in numerous publications in high impact journals. The clarity and depth of the experimental section will be useful for students and researchers working in this field.
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