Development of New Radical Cascades and Multi-Component Reactions

Application to the Synthesis of Nitrogen-Containing Heterocycles

  • Marie-Helene Larraufie
Part of the Springer Theses book series (Springer Theses)

Table of contents

  1. Front Matter
    Pages i-xxii
  2. N-acylcyanamides as New Partners in Radical Cascades: Synthesis of Polycyclic Quinazolinones and Guanidines

    1. Front Matter
      Pages 1-1
    2. Marie-Hélène Larraufie
      Pages 3-37
    3. Marie-Hélène Larraufie
      Pages 79-136
  3. Visible-light Photoreductive Catalysis for an Eco-compatible Generation of Radicals

    1. Front Matter
      Pages 137-137
    2. Marie-Hélène Larraufie
      Pages 195-226
  4. New developments in Aryl–Aryl Couplings via Palladium/Norbornene Dual Catalysis: Synthesis of Phenanthridines and Phenanthrenes

    1. Front Matter
      Pages 227-227
    2. Marie-Hélène Larraufie
      Pages 295-324
  5. Back Matter
    Pages 325-326

About this book

Introduction

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. 

Keywords

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

Authors and affiliations

  • Marie-Helene Larraufie
    • 1
  1. 1.Department of Biological Sciences Department of ChemistryColumbia University, The Stockwell LaborNew YorkUSA

Bibliographic information

  • DOI https://doi.org/10.1007/978-3-319-01324-4
  • Copyright Information Springer International Publishing Switzerland 2014
  • Publisher Name Springer, Cham
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-3-319-01323-7
  • Online ISBN 978-3-319-01324-4
  • Series Print ISSN 2190-5053
  • Series Online ISSN 2190-5061
  • About this book