New water-soluble Schiff base ligands based on β-cyclodextrin for aqueous biphasic hydroformylation reaction

Abstract

The synthesis of water-soluble rhodium(I) salicylaldiminato and salicylhydrazonic complexes has been achieved employing two preparative routes. Schiff base condensation between 6A-deoxy-6A-amino-β-CD or 6A-deoxy-6A-hydrazino-β-CD and 5-sodiosulfonato-2-hydroxybenzaldehyde (sulfonated salicylaldehyde) (1) or 5-sodiosulfonato-3-tert-butyl-2-hydroxybenzaldehyde (sulfonated tBu-salicylaldehyde) (2) led to the formation of the corresponding imine or hydrazone ligands (3, 4, 5 and 6). Reaction of [Rh(COD)2+BF4-] with these new ligands in an alkaline solution formed the corresponding rhodium complexes quantitatively. These rhodium(I) complexes could also be prepared in one-pot by mixing, in stoichiometric proportions, the modified β-CDs with the sulfonated salicylaldehyde and with the rhodium precursor in an alkaline solution at room temperature. These rhodium complexes were applied as catalysts in the aqueous biphasic hydroformylation of 1-decene as a model reaction.