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Reaction of Pyridine‐ N ‐Oxides with Tertiary sp 2 ‐ N ‐Nucleophiles: An Efficient Synthesis of Precursors for N ‐(Pyrid‐2‐yl)‐Substituted N ‐Heterocyclic Carbenes
Author(s) -
Bugaenko Dmitry I.,
Yurovskaya Marina A.,
Karchava Alexander V.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001063
Subject(s) - chemistry , pyridinium , pyridine , regioselectivity , nucleophile , medicinal chemistry , surface modification , electrophile , combinatorial chemistry , organic chemistry , catalysis
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 S N Ar‐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.