Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 11-12, Pages 1906-1916Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600628
Keywords
arylation; catalysis; copper; nitrogen ligands; nucleophiles
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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 I 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.
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