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Copper, Silver and Sodium Salt‐Mediated Quaternization by Arylation: Syntheses of N‐Heterocyclic Carbene Precursors and 6‐ H ‐Phenanthridine Derivatives
Author(s) -
Shen Wenqi,
Li Jing,
Zhang Caiyun,
Shi Min,
Zhang Jun
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600563
Subject(s) - carbene , phenanthridine , chemistry , deprotonation , salt (chemistry) , intramolecular force , organic chemistry , quinoline , medicinal chemistry , polymer chemistry , combinatorial chemistry , catalysis , ion
We have developed a Cu II ‐, Ag I ‐, and NaOTf‐mediated intramolecular quaternization by arylation reactions to synthesize a variety of N‐heterocyclic carbene (NHC) precursors with a benzene‐fused backbone. The methodology also provides a convenient alternative route for the synthesis of 6‐ H ‐phenanthridine derivatives. A novel silver–NHC complex was prepared by treatment of Ag 2 O with the free carbene, which was in situ prepared from the deprotonation of a representative quinazolinonium salt.