Synthesis,characterization and catalytic activity of novel Co(II) and Pd(II)‐perfluoroalkylphthalocyanine in fluorous biphasic system; benzyl alcohol oxidation

Tetrakisheptadecafluorononyl] substituted phthalocyanine complexes were prepared by template synthesis from 4‐(heptadecafluorononyloxy)phthalonitrile with Co(CH₃COO)^·₂H₂O or PdCl₂ in 2‐N, N‐dimethylaminoethanol. The corresponding phthalonitrile was obtained from heptadecafluorononan‐1‐ol and 4‐nitrophthalonitrile with K₂CO₃ in DMF at 50 °C. The structures of the compounds were characterized by elemental analysis, FTIR, UV–vis and MALDI‐TOF MS spectroscopic methods. Metallophthalocyanines are soluble in fluoroalkanes such as perfluoromethylcyclohexane (PFMCH). The complexes were tested as catalysts for benzyl alcohol oxidation with tert‐butylhydroperoxide (TBHP) in an organic–fluorous biphasic system (n‐hexane–PFMCH). The oxidation of benzyl alcohol was also tested with different oxidants, such as hydrogen peroxide, m‐chloroperoxybenzoic acid, molecular oxygen and oxone in n‐hexane–PFMCH. TBHP was found to be the best oxidant for benzyl alcohol oxidation since higher conversion and selectivity were observed when this oxidant was used. Copyright © 2008 John Wiley & Sons, Ltd.