Tunable, Chemoselective Amination via Silver Catalysis

Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C–H bond or...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 46; pp. 17238 - 17241
Main Authors Rigoli, Jared W, Weatherly, Cale D, Alderson, Juliet M, Vo, Brian T, Schomaker, Jennifer M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2013
Amer Chemical Soc
Subjects
Amination
Amines - chemical synthesis
Amines - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Molecular Conformation
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Silver - chemistry
FUNCTIONALIZATION
INTERMOLECULAR AMINATION
HYDROCARBONS
REDUCTION
AZIRIDINATION
PORPHYRINS
COMPLEXES
AMIDATION
C-H AMINATION
MOLECULES
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Summary:Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C–H bond or add it directly to a CC bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C–H insertion by manipulating the coordination geometry of the active catalysts.
Bibliography:NIH RePORTER
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja406654y