Abstract
A series of novel ionic liquid-supported Schiff bases have been prepared from the condensation of aromatic aldehydes with the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate. The as-prepared ionic liquid-supported salicyladehyde Schiff base L3 was further investigated as a ligand for the Pd-catalyzed Suzuki-Miyaura coupling reaction under air in ethanol solution, giving biaryls in good to excellent yields. The PdCl2/ligand L3 catalytic system could be reused at least 5 times without losing its activity.
Highlights
Transition-metal-catalyzed cross-coupling is a versatile and highly useful transformation, which yields a variety of organic compounds
We wish to report the use of ionic liquid-supported Schiff base as the palladium (II) ligand to demonstrate their suitability in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions
The ligands L1-L6 of ionic liquid supported Schiff base were readily prepared by the condensation of aromatic aldehydes with the functionalized ionic liquid 1-(2-aminoethyl)-3methylimidazolium hexafluorophosphate (Scheme 1)
Summary
Transition-metal-catalyzed cross-coupling is a versatile and highly useful transformation, which yields a variety of organic compounds. We wish to report the use of ionic liquid-supported Schiff base as the palladium (II) ligand to demonstrate their suitability in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. To evaluate the activity of the catalyst formed in situ from ligand L1-L6 and PdCl2 in Suzuki-Miyaura reaction, the coupling reaction of 4-iodoanisole with phenylboronic acid has been chosen as a model reaction (Table 1).
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