Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N‑Containing Molecules from Alkenes and Alkynes

Nitrogen (N) is ubiquitously found in bioactive molecules, pharmaceutical agents, and organic functional materials. Accordingly, development of new C–N bond-forming catalysis has been one of the long-standing research subjects in synthetic organic chemistry. In this Perspective, recent advances in h...

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Published inJournal of the American Chemical Society Vol. 144; no. 2; pp. 648 - 661
Main Authors Hirano, Koji, Miura, Masahiro
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 19.01.2022
Subjects
alkenes
alkynes
amination
catalytic activity
Lewis acids
nitrogen
organic chemistry
reaction mechanisms
stereoselective synthesis
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Summary:Nitrogen (N) is ubiquitously found in bioactive molecules, pharmaceutical agents, and organic functional materials. Accordingly, development of new C–N bond-forming catalysis has been one of the long-standing research subjects in synthetic organic chemistry. In this Perspective, recent advances in highly selective amination reactions with electrophilic amination reagents are described: by taking advantage of the concept of nitrogen umpolung, otherwise challenging aminofunctionalizations, such as hydroamination, aminoboration, and carboamination, of readily available feedstock-like alkenes and alkynes are possible, giving densely functionalized complex and often chiral alkylamines with high selectivity. The scope, limitations, and reaction mechanism are briefly summarized.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.1c12663