Copper-Catalyzed Electrophilic Amination of sp2 and sp3 CH Bonds

Zusatztext

This thesis reports on the latest developments in the direct amination of various C-H bonds using an H-Zn exchange/electrophilic amination strategy as a rapid and powerful method for accessing a variety of functionalized amines. The authors were able to achieve 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. With such a one-pot procedure, the synthesis of various amines from C-H bonds has been achieved, including a-amination of esters, amides, and phosphonates. The widespread presence of C-N bonds in biologically and pharmaceutically important compounds continues to drive the development of new C-N bond-forming transformations. Among the various strategies pursued, electrophilic amination is an important synthetic approach for the direct formation of C-N bonds. Direct amination of heteroaromatic and aromatic C-H bonds has also been developed in good to high yields. Thanks to their mild reactivity, organozinc reagents offer good compatibility with different functional groups, such as esters, amides, and halides.

Autorenportrait

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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