Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H Bonds

Stacey L. McDonald

• Publisher: Springer
• Year: 2016
• Print ISBN:
  9783319388779
• eBook ISBN:
  9783319388786
• Topic: Physical Sciences
• Subtopic: Clinical Chemistry

This thesis reports the latest developments in the direct amination of various C?H bonds using an H?Zn exchange/electrophilic amination strategy.  McDonald and co-workers reveal this approach to be a rapid and powerful method for accessing a variety of functionalized amines.

The material outlined in this book shows how McDonald achieved C?H zincation using strong, non-nucleophilic zinc bases and subsequent electrophilic amination of the corresponding zinc carbanions with copper as a catalyst and O-benzoylhydroxylamines as the electrophilic nitrogen source.

McDonald's findings are of relevance to medicinal chemistry, drug discovery and materials science. Her thesis is a source of inspiration for scientists entering the field and students beginning their PhD in a related area. 

Table of contents

• Supervisor’s Foreword
• Abstract
• Parts of this thesis have been published in the following journal articles:
• Acknowledgements
• Contents
• Abbreviations
• List of Figures
• List of Tables
• List of Schemes
• 1 Electrophilic Amination for the Synthesis of Alkyl and Aryl Amines
• 2 Selective α-Amination and α-Acylation of Esters and Amides via Dual Reactivity of O-Acylhydroxylamines Toward Zinc Enolates
• 3 Copper-Catalyzed α-Amination of Phosphonates and Phosphine Oxides: A Direct Approach to α-Amino Phosphonic Acids and Derivatives
• 4 Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C–H Zincation
• Curriculum Vitae