Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 52, Pages 17606-17615Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404275
Keywords
aryl ethers; copper; cross-coupling; N ligands; structure-activity relationships
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Funding
- AstraZeneca UK
- Engineering and Physical Sciences Research Council [EP/K039202/1] Funding Source: researchfish
- EPSRC [EP/K039202/1] Funding Source: UKRI
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The use of picolinic acid amide derivatives as an effective family of bidentate ligands for copper-catalysed aryl ether synthesis is reported. A fluorine-substituted ligand gave good results in the synthesis of a wide range of aryl ethers. Even bulky phenols, known to be very challenging substrates, were shown to react with aryl iodides with excellent yields using these ligands. At the end of the reaction, the first examples of end-of-life Cu species were isolated and identified as Cu-II complexes with several of the anionic ligands tested. A preliminary mechanistic investigation is reported that suggests that the substituents on the ligands might have a crucial role in determining the redox properties of the metal centre and, consequently, its efficacy in the coupling process. An understanding of these effects is important for the development of new efficient and tunable ligands for copper-based chemistry.
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