Synthesis of 3-aryl-5-t-butylsalicylaldehydes and their chiral Schiff base compounds

Article abstract of DOI:10.1080/00397910701572423

Six meta-substituted salicylaldehyde compounds have been prepared in 68-90% yields by the Suzuki-Miyaura coupling reaction using 3-bromo-5-t- butylsalicylaldehyde (1a) and arylboronic acids (2a-f) as reactants. Among the obtained products, 3-(4-fluorophenyl)-5-t-butylsalicylaldehyde (3b), 3-(4-methylphenyl)-5-t-butylsalicylaldehyde (3d), 3-(1-naphthyl)-5-t- butylsalicylaldehyde (3e), and 3-(2-naphthyl)-5-t-butylsalicylaldehyde (3f) have not been reported so far. A series of new Schiff base ligands (L1-L10) were obtained in 51-89% yields from these salicylaldehyde derivatives. Copyright Taylor & Francis Group, LLC.