Taming Troublesome Suzuki-Miyaura Reactions in Water Solution of Surfactants by the Use of Lecithin: A Step Beyond the Micellar Model

Abstract

<div>The use of water solutions of industrial and designer surfactants enables performing a wide variety of chemical transformation on hydrophobic precursors. Mostly reactions </div><div>are clean, fast and efficient with vast benefits for overall sustainability. The widespread adoption of such methods is somewhat hampered by a lack of generality in the case of troublesome substrates and scaling up. The common literature solution for such issues is the use of small amounts of organic solvents. We here show that the use of a mixture of L-α-lecithin and Tween 80 is a preferable solution enabling the taming of particularly troublesome reactions, where even the cosolvent approach fails. The strong reduction of all interface tensions characterizing such complex multiphase systems is key to the results achieved. The protocol, applied to Suzuki-Miyaura couplings, allows to obtain complete reactions conversion at room temperature within one hour, is general and scalable from milligrams to up to 10 grams without further adjustments.</div>