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In this dissertation, Marie-Hélène Larraufie develops original
radical and pallado-catalyzed methodologies to enable the synthesis
of 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, Larraufie expands the scope of visible
light photoredox catalysis to the ring opening of epoxides and
aziridines, thus providing new sustainable alternatives for the
generation of radicals. Furthermore, in a collaborative effort with
the Catellani group, the author investigates dual
palladium/norbornene catalysis. First, she develops a C-amination
coupling variant of the Catellani reaction with unprotected amines
which provides an expeditious route to phenanthridines. Then, she
examines the influence of the chelating effect on Pd(IV)
intermediates reactivity 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.Â
In this dissertation, Marie-Helene Larraufie develops original
radical and pallado-catalyzed methodologies to enable the synthesis
of 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, Larraufie expands the scope of visible
light photoredox catalysis to the ring opening of epoxides and
aziridines, thus providing new sustainable alternatives for the
generation of radicals. Furthermore, in a collaborative effort with
the Catellani group, the author investigates dual
palladium/norbornene catalysis. First, she develops a C-amination
coupling variant of the Catellani reaction with unprotected amines
which provides an expeditious route to phenanthridines. Then, she
examines the influence of the chelating effect on Pd(IV)
intermediates reactivity 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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