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

作者：Dauchy Maxime; Ferreira Michel; Leblond Jerome; Bricout Herve; Tilloy Sebastien; Smith Gregory S; Monflier Eric

来源：Pure and Applied Chemistry, 2018, 90(5): 845-855.

DOI：10.1515/pac-2017-1205

<jats:title>Abstract</jats:title>
<jats:p>The synthesis of water-soluble rhodium(I) salicylaldiminato and salicylhydrazonic complexes has been achieved employing two preparative routes. Schiff base condensation between 6<jats:sup>A</jats:sup>-deoxy-6<jats:sup>A</jats:sup>-amino-β-CD or 6<jats:sup>A</jats:sup>-deoxy-6<jats:sup>A</jats:sup>-hydrazino-β-CD and 5-sodiosulfonato-2-hydroxybenzaldehyde (sulfonated salicylaldehyde) (<jats:bold>1</jats:bold>) or 5-sodiosulfonato-3-<jats:italic>tert</jats:italic>-butyl-2-hydroxybenzaldehyde (sulfonated <jats:sup><jats:italic>t</jats:italic></jats:sup>Bu-salicylaldehyde) (<jats:bold>2</jats:bold>) led to the formation of the corresponding imine or hydrazone ligands (<jats:bold>3</jats:bold>, <jats:bold>4</jats:bold>, <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold>). Reaction of [Rh(COD)<jats:sub>2</jats:sub><jats:sup>+</jats:sup>BF<jats:sub>4</jats:sub><jats:sup>−</jats:sup>] 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.</jats:p>

• 出版日期2018-4