Micellar catalysis beyond the hydrophobic effect: Efficient palladium catalyzed Suzuki-Miyaura coupling of water and organic solvent insoluble pigments with food grade surfactants

Abstract

Micellar catalysis is having a dramatic impact in improving the sustainability of a wide variety of chemical transformations, including most of the popular palladium mediated carbon–carbon and carbon–nitrogen bond forming reactions. The Suzuki-Miyaura coupling is one of the earliest examples of micellar catalyzed reactions and it is still a very much active research field even at industrial scale. So far, micellar catalysis proved particularly efficient in enabling the high yield, low catalyst loading and mild reaction condition coupling of hydrophobic reagents in a water solution of selected surfactants. In this paper we show that the use of aqueous solutions of a mixture of food grade lecithin and the industrial surfactant Tween 80 not only enables efficient coupling in water of hydrophobic chemicals, but also provides a very resourceful tool for the functionalization of water and organic solvent insoluble pigments of interest for the dye and printed electronic industries.