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Chemistry - Organic Chemistry | Development of New Radical Cascades and Multi-Component Reactions - Application to the Synthesis

Development of New Radical Cascades and Multi-Component Reactions

Application to the Synthesis of Nitrogen-Containing Heterocycles

Series: Springer Theses

Larraufie, Marie-Helene

2014, XXII, 326 p. 517 illus., 42 illus. in color.

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  • Nominated as an outstanding Ph.D. thesis by the IPCM Université Pierre et Marie Curie, France
  • Honored with the French Chemical Society (SCF) - Organic Chemistry Section Ph. D. award for 2011
  • Presents detailed and clear experimental sections useful for students in the field
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. 

Content Level » Research

Keywords » Aromatic Homolytic Substitution - Catellani Reaction - Cyanamides - Guanidines - Ortho Effect - Palladium IV - Photoredox Catalysis - Quinazolinones - Radical Cascades

Related subjects » Catalysis - Organic Chemistry - Theoretical and Computational Chemistry

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