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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.
List of contents
Electrophilic amination for the synthesis of alkyl and aryl amines.- Selective -amination and -acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates.- Copper-catalyzed -amination of phosphonates and phosphine oxides: a direct approach to -amino phosphonic acids and derivatives.- Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C-H Zincation.
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.
Summary
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.
