1st Edition

The Chemistry of Ynamides Development, Syntheses, and Applications in Organic Synthesis

By Gwilherm Evano, Junfeng Zhao Copyright 2024
    720 Pages 85 Color & 504 B/W Illustrations
    by Jenny Stanford Publishing

    720 Pages 85 Color & 504 B/W Illustrations
    by Jenny Stanford Publishing

    Ynamides contain a triple bond directly connected to a nitrogen atom that bears an electron-withdrawing group. They represent an especially useful and emerging class of reagents, notably because of their strongly polarized triple bond, which enables the development of unique chemical transformations. While they were discovered by Viehe in 1972, their chemistry has remained little investigated and the renaissance of ynamide chemistry started at the dawn of the 20th century with the development of efficient methods for their synthesis. Since then, ynamide chemistry has developed at a remarkably high rate, notably in the past 20 years. Although there are several reviews on ynamide chemistry, most of them are out of date or only focus on special aspects of ynamide chemistry and there is no book about ynamide chemistry yet. Thus, a comprehensive book on ynamide chemistry would be timely and is highly needed.

    This book covers all aspects of ynamide chemistry, including their discovery, their syntheses, their application in heterocyclic chemistry, natural product synthesis, and organometallic chemistry, and their use as coupling reagents. It provides a systematic and comprehensive overview on ynamide chemistry for the researchers in this field, general readers interested in synthesis, and those who want to enter this field and need a comprehensive and up-to-date overview. Undoubtedly, this book will play a key role in connecting the past with the future to further foster the development of ynamide chemistry.

    1. The Discovery of Ynamines and Ynamides: A Historical Perspective

    Gwilherm Evano


    2. Synthesis of Ynamides

    Mounsef Lahboubi and Gwilherm Evano


    3. The Cationic Chemistry of Ynamides, Useful Precursors of Keteniminium Ions

    Pierre Thilmany and Gwilherm Evano


    4. The Anionic Chemistry and Carbometallation of Ynamides

    Alaâ Saadane and Gwilherm Evano


    5. Radical Reactions of Ynamides

    Qiaolan Yang, Diksha Singh, Vincent Debrauwer, Vincent Bizet, and Nicolas Blanchard


    6. Transition Metal-Catalyzed Reactions of Ynamides

    Manash Protim Gogoi, Shubham Dutta, Shashank Shandilya, and Akhila Kumar Sahoo


    7. Ynamides as Precursors of Carbenes and Carbenoids

    Joshua D. Priest and Paul W. Davies


    8. Reversal of Regioselectivity in the Chemistry of Ynamides

    Long-Wu Ye


    9. Pericyclic Reactions of Ynamides

    Lénaic Rummler, Nicolas Brach, Pierre Delmée, Logan Charton, Vincent Bizet, and Nicolas Blanchard


    10. Ynamides in Multicomponent Reactions

    Linwei Zeng and Sunliang Cui


    11. Ynamides as Racemization-Free Coupling Reagents for Amide and Ester Bond Formation

    Chunyu Han, Tao liu, Xue Zhang, and Junfeng Zhao


    12. Ynamides in the Synthesis of Natural/Biologically Relevant Products

    Cédric Theunissen


    Gwilherm Evano studied chemistry at the École Normale Supérieure in Paris, France, and received his PhD from the Université Pierre et Marie Curie in 2002 under the supervision of Profs. François Couty and Claude Agami. After postdoctoral studies with Prof. James S. Panek at Boston University, working on natural product synthesis, he joined the CNRS as an associate professor in 2004. He then moved to the Université libre de Bruxelles, Belgium, where he became the head of the Laboratory of Organic Chemistry in 2012. His research focuses on natural/bioactive product synthesis, copper catalysis, photoredox catalysis, organometallic chemistry, and the chemistry of ynamides and other heteroatom-substituted alkynes as well as reactive intermediates.


    Junfeng Zhao obtained his bachelor’s and master’s degrees from Beijing Normal University and Central China Normal University in 2001 and 2005, respectively. After one year of PhD candidate study at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, he moved to Singapore to continue his PhD study at Nanyang Technological University and received his PhD in 2010. After postdoctoral research at Nanyang Technological University, University of Bonn, and University of Muenster from 2010 to 2013, Dr Zhao joined the University of Hong Kong as a research assistant professor. He started his independent career at Jiangxi Normal University as a full professor in 2014 and stayed there until 2020. In 2021, his research group moved to Guangzhou Medical University. Dr Zhao’s research interest focuses on the synthesis and modification of peptides and proteins as well as their application in drug discovery.