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Nitrogen Ligands in Copper‐Catalyzed Arylation of Phenols: Structure/Activity Relationships and Applications
Author(s) -
Ouali Armelle,
Spindler JeanFrancis,
Jutand Anny,
Taillefer Marc
Publication year - 2007
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.200600628
Subject(s) - chemistry , ligand (biochemistry) , imine , pyridine , denticity , nucleophile , combinatorial chemistry , catalysis , yield (engineering) , rational design , copper , organic chemistry , nanotechnology , crystal structure , receptor , biochemistry , materials science , metallurgy
Abstract In spite of the importance of ligand/copper‐catalyzed arylations of nucleophiles in organic chemistry, the structural and electronic features that make a ligand efficient in these reactions have not been determined until now. In this work, several bidentate ligands involving pyridine and/or imine nitrogen binding sites such as our lead ligand 1 have been synthesized, and tested in phenol arylations with a view to highlight relationships between the structure of the chelates and their efficacy. This study allowed us to more precisely define the role of each type of N ‐ binding site during the catalytic process, and to discover new efficient ligands. Among them, the iminopyridine 6a , which is cheap and easy‐to‐prepare in high yield, is very attractive for industrial applications. Some examples of its field of application are presented here. In the future, the development of this work could allow a more rational design of efficient ligands in arylation reactions, without resorting to classical ligand screening.