Premium
Palladium‐Catalyzed Selective CH Activation: A Simple Method to Synthesize C‐3 Site Arylated Quinoline Derivatives
Author(s) -
He Yongqin,
Wu Zhaoyang,
Ma Chaowei,
Zhou Xiaoqiang,
Liu Xingxing,
Wang Xiajun,
Huang Guosheng
Publication year - 2016
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.201500763
Subject(s) - chemistry , palladium , catalysis , quinoline , reagent , combinatorial chemistry , selectivity , ligand (biochemistry) , organic chemistry , biochemistry , receptor
A novel protocol for the synthesis of 3‐arylated quinoline derivatives has been developed using silver carbonate (Ag 2 CO 3 ) and dioxygen (O 2 ) as the oxidants. In this method, quinolines acting as the parent reagent react with arenes under palladium acetate [Pd(OAc) 2 ] catalysis along with 1‐adamantanecarboxylic acid (Adm). The combination of the 1‐adamantanecarboxylic acid ligand and the palladium catalyst is found to be an essential factor for achieving high activity and selectivity, and allows a wide range of 3‐arylquinoline derivatives to be obtained in high yields. Moreover, a relevant mechanism is proposed, revealing that un der the palladium(II) catalysis a migratory insertion to C‐3H of quinolines and insertion to the CH of arenes are key steps in this reaction. Mild reaction conditions and high selectivity of the reactive site provide potential for promising applications in drug discovery and functional materials.