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

  • Book
  • © 2016

Overview

Authors:
  1. Stacey L. McDonald

    1. Dept. of Chemistry, Duke University Dept. of Chemistry, Durham, NC, USA

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  • Nominated as an outstanding PhD thesis by Duke University
  • Provides a comprehensive review of electrophilic aminations using O-benzoylhydroxylamines
  • Presents results which are relevant for medicinal chemistry, drug discovery and materials science
  • 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-xxiii
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  2. Electrophilic Amination for the Synthesis of Alkyl and Aryl Amines

    • Stacey L. McDonald
    Pages 1-23

  3. Selective α-Amination and α-Acylation of Esters and Amides via Dual Reactivity of O-Acylhydroxylamines Toward Zinc Enolates

    • Stacey L. McDonald
    Pages 25-60

  4. Copper-Catalyzed α-Amination of Phosphonates and Phosphine Oxides: A Direct Approach to α-Amino Phosphonic Acids and Derivatives

    • Stacey L. McDonald
    Pages 61-95

  5. Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C–H Zincation

    • Stacey L. McDonald
    Pages 97-142

  6. Back Matter

    Pages 143-144
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Keywords

About this book

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. 

Authors and Affiliations

  • Dept. of Chemistry, Duke University Dept. of Chemistry, Durham, NC, USA

    Stacey L. McDonald

About the author

Born and raised in South Carolina, Stacey McDonald completed her B.S. in Chemistry from Wofford College in 2009. She then matriculated into the Chemistry Department at Duke University to pursue her Ph.D. in Organic Chemistry. While at Duke, Stacey's research focused on organic synthesis and methodology development for electrophilic aminations. She successfully defended her Ph.D. in March 2015. Stacey is currently working as a Postdoctoral Fellow at the University of North Carolina - Chapel Hill in the lab of Jeff Aubé.

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