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Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

New Developments and Mechanistic Studies

  • Book
  • © 2014

Overview

Authors:
  1. Antoine Simonneau

    1. Paris Institute of Molecular Chemistry, University Pierre and Marie Curie, Paris, France

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  • Nominated as an Outstanding Ph.D. thesis by Université Pierre et Marie Curie, France
  • Establishes higher molecular complexity in products of new gold catalyzed cyclization reactions and follow-up chemistry
  • Questions the occurrence of gold acetylides and sigma, pi complexes in gold-catalyzed cycloisomerization reactions involving free alkynes
  • Includes supplementary material: sn.pub/extras

Part of the book series: Springer Theses (Springer Theses)

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Table of contents (4 chapters)

  1. Front Matter

    Pages i-xxii
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  2. Gold- and Platinum-Catalyzed Reactions of Enynes

    • Antoine Simonneau
    Pages 1-42

  3. New Advances in the Gold-Catalyzed Cycloisomerization Reactions of Enynes: 1,5-hydride Shifts and Access to Ketomacrolactones

    • Antoine Simonneau
    Pages 43-84

  4. Synthesis of Polyconjugated Bis-Enones Through a Gold-Catalyzed 1,3-Acyloxy Migration-Cyclization-1,5-Acyl Shift Cascade Reaction

    • Antoine Simonneau
    Pages 85-117

  5. Tracking Gold Acetylides in Gold(I)-Catalyzed Cycloisomerization Reactions of 1,6-Enynes

    • Antoine Simonneau
    Pages 119-147

  6. Back Matter

    Pages 149-245
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Keywords

About this book

Antoine Simonneau's thesis highlights the development of new cycloisomerization reactions through the activation of alkynes with gold complexes. First Simonneau describes 1,6-enynes and their direct conversion into allenes through 1,5-hydride or ester migration processes. The author and his team used appropriate propargylic functional groups to achieve this conversion. This study shows that O-tethered 1,6-enynes carrying a strained cycloalkane at the propargylic position could undergo a cyclopropanation/ring expansion cascade reaction. The author employed this rearrangement as the starting point in the design of a new macro cycle synthesis. The next part of the thesis focuses on the cycloisomerization of diynes involving as the first step of the process the rearrangement of one alkyne partner into an allene thanks to a gold-catalyzed 1,3-shift of a propargylic ester. The thesis discloses a new cycloisomerization pattern featuring a 1,5-carbonyl transfer, giving rise to unprecedented cross-conjugated diketones. In the final part of the research, Simmoneau investigates the gold-catalyzed cycloisomerization mechanism of 1,6-enynes and questions the intermediacy of gold acetylides. By the means of NMR and mass spectrometry analysis, theoretical treatment and solution experiments, it was possible to rule out the involvement of these species in the catalytic cycle. This thesis has led to a number of publications in high-impact journals.

Authors and Affiliations

  • Paris Institute of Molecular Chemistry, University Pierre and Marie Curie, Paris, France

    Antoine Simonneau

About the author

Antoine Simonneau obtained his Ph. D. under the guidance of Profs. Louis Fensterbank and Max Malacria at the Université Pierre et Marie Curie (Paris). At this time he was involved in the development of new cycloisomerization reactions under gold catalysis and mechanistic studies. He is currently a Humboldt postdoctoral fellow in the laboratory of Prof. Martin Oestreich at the Technische Universität of Berlin, where he is working on catalysis with main group electrophiles.

Bibliographic Information

  • Book Title: Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

  • Book Subtitle: New Developments and Mechanistic Studies

  • Authors: Antoine Simonneau

  • Series Title: Springer Theses

  • DOI: https://doi.org/10.1007/978-3-319-06707-0

  • Publisher: Springer Cham

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: Springer International Publishing Switzerland 2014

  • Hardcover ISBN: 978-3-319-06706-3Published: 11 June 2014

  • Softcover ISBN: 978-3-319-36097-3Published: 10 September 2016

  • eBook ISBN: 978-3-319-06707-0Published: 21 May 2014

  • Series ISSN: 2190-5053

  • Series E-ISSN: 2190-5061

  • Edition Number: 1

  • Number of Pages: XXII, 245

  • Number of Illustrations: 399 b/w illustrations, 5 illustrations in colour

  • Topics: Organometallic Chemistry, Catalysis, Industrial Chemistry/Chemical Engineering

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