Reaction of Pyridine‐N‐Oxides with Tertiary sp2‐N‐Nucleophiles: An Efficient Synthesis of Precursors for N‐(Pyrid‐2‐yl)‐Substituted N‐Heterocyclic Carbenes

N‐(Pyrid‐2‐yl)‐substituted azolium and pyridinium salts, precursors for hybrid NHC‐containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH‐functionalization of pyridine‐N‐oxides with substituted imidazoles, thiazoles, and pyridine. Unlike the traditional SNAr‐...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-12, Vol.362 (24), p.5777-5782
Main Authors: Bugaenko, Dmitry I., Yurovskaya, Marina A., Karchava, Alexander V.
Format: Article
Language:English
Subjects:
Amination
Benzodiazepines
Carbenes
C−H functionalization
Deoxygenation
Imidazole
N-Heterocyclic carbenes
Nitrogen Heterocycles
Nucleophiles
Precursors
Pyridine N-oxide
Regioselectivity
Substitutes
Substrates
Synthesis
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Summary:N‐(Pyrid‐2‐yl)‐substituted azolium and pyridinium salts, precursors for hybrid NHC‐containing ligands, were obtained with excellent regioselectivity, employing a deoxygenative CH‐functionalization of pyridine‐N‐oxides with substituted imidazoles, thiazoles, and pyridine. Unlike the traditional SNAr‐based methods, this approach provides high yields for substrates bearing substituents of different electronic nature. The utility of azolium and pyridinium salts thus prepared was also highlighted by the synthesis of pyridyl‐substituted imidazolyl‐2‐thione, benzodiazepine as well as 2‐aminopyridines.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001063