Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

Over the past few years, CuH‐catalyzed hydroamination has been discovered and developed as a robust and conceptually novel approach for the synthesis of enantioenriched secondary and tertiary amines. The success in this area of research was made possible through the large body of precedent in copper...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-01, Vol.55 (1), p.48-57
Main Authors: Pirnot, Michael T., Wang, Yi-Ming, Buchwald, Stephen L.
Format: Article
Language:English
Subjects:
Alkenes
Alkenes - chemistry
Alkynes
Alkynes - chemistry
Amination
Amines
Amines - chemical synthesis
Amines - chemistry
asymmetric catalysis
Catalysis
chiral amine synthesis
Copper
Copper - chemistry
copper catalysis
copper(I) hydride
Esters
hydroamination
Hydroxylamine
Molecular Structure
Organometallic Compounds - chemistry
Stereoisomerism
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Summary:Over the past few years, CuH‐catalyzed hydroamination has been discovered and developed as a robust and conceptually novel approach for the synthesis of enantioenriched secondary and tertiary amines. The success in this area of research was made possible through the large body of precedent in copper(I) hydride catalysis and the well‐explored use of hydroxylamine esters as electrophilic amine sources in related copper‐catalyzed processes. This Minireview details the background, advances, and mechanistic investigations in CuH‐catalyzed hydroamination. Mild and abundant: CuH‐catalyzed hydroamination has recently been developed as a viable method for synthesizing a broad range of chiral aliphatic amines in excellent efficiencies and enantioselectivites. This Minireview highlights advancements made in this area of catalysis along with the precedent that has led to these discoveries.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201507594