Development of New Radical Cascades and Multi-Component by Marie-Helene Larraufie

By Marie-Helene Larraufie

In this dissertation, Marie-Hélène Larraufie develops unique radical and pallado-catalyzed methodologies to let the synthesis of a number of sessions of bioactive nitrogen-containing heterocycles. New radical cascades applying the N-acylcyanamide moiety supply elementary routes to quinazolinones and guanidines, in addition to new insights into the mechanism of homolytic fragrant substitutions. In parallel, Larraufie expands the scope of obvious gentle photoredox catalysis to the hoop starting of epoxides and aziridines, hence delivering new sustainable choices for the new release of radicals. in addition, in a collaborative attempt with the Catellani staff, the writer investigates twin palladium/norbornene catalysis. First, she develops a C-amination coupling version of the Catellani response with unprotected amines which gives an expeditious path to phenanthridines. Then, she examines the impact of the chelating influence on Pd(IV) intermediates reactivity with assistance from experimental experiences and DFT calculations. The paintings during this thesis has ended in a number of guides in excessive influence journals.The readability and intensity of the experimental part should be precious for college kids and researchers operating during this box.

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Since Crich has demonstrated that dihydro products are not oxidized rapidly in air [118], the maximum yields reachable would be 50 %. This pathway was consequently dismissed. The stability of dihydro products also excludes the direct H transfer from Bu3SnH to sigma complex 96. 24 1 Bibliographical Backgrounds (a) (b) (c) (d) Fig. 37 Rearomatization through abstraction of hydrogen from cyclohexadienyl radical by oxygen Fig. 38 First mechanistic proposal: disproportionation The second mechanistic proposal suggested that Bu3SnH could act as a hydride base and deprotonate sigma radical 96 to lead to radical anion 99, Bu3Sn+ and H2.

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