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

Chiara Ceriani,Luca Beverina,Mauro Sassi,Erika Ghiglietti,Sara Mattiello

doi:10.1021/acs.oprd.0c00285

Chiara Ceriani, Luca Beverina + Show 3 more

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https://doi.org/10.1021/acs.oprd.0c00285

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Abstract

The use of water solutions of industrial and designer surfactants enables performing a wide variety of chemical transformations on hydrophobic precursors. Most reactions are clean, fast, and effici...

Highlights

The development of improved synthetic methods offering selectivity, high yield, and short reaction times while providing moderate or no heating is a cornerstone of modern sustainable chemistry.[1,2] the need for organic solvents remains the elephant in the room.[3,4] Despite the obvious benefits, their replacement with water in homogeneous phase reactions is troublesome as the vast majority of fine chemicals and/or precursors are water insoluble
The literature shows that the addition of surfactants to water can drastically change such a scenario.[5−9] Several different chemical processes can be profitably performed in water with high yield, irrespective to the solubility of reagents and products.[10−14] Gathered under the banner of “micellar catalysis” (MC), such methods witnessed an enormous boost in scope, generality, and synthetic usefulness in the last 10 years, even at the industrial scale.[15−18]
We identified several Suzuki− Miyaura (SM) coupling reactions showing reproducibility issues; some of which are shown in Scheme 1

Summary

Introduction

The development of improved synthetic methods offering selectivity, high yield, and short reaction times while providing moderate or no heating is a cornerstone of modern sustainable chemistry.[1,2] the need for organic solvents remains the elephant in the room.[3,4] Despite the obvious benefits, their replacement with water in homogeneous phase reactions is troublesome as the vast majority of fine chemicals and/or precursors are water insoluble. The literature shows that the addition of surfactants to water can drastically change such a scenario.[5−9] Several different chemical processes can be profitably performed in water with high yield, irrespective to the solubility of reagents and products.[10−14] Gathered under the banner of “micellar catalysis” (MC), such methods witnessed an enormous boost in scope, generality, and synthetic usefulness in the last 10 years, even at the industrial scale.[15−18]. Co-localization and hydrophobic effects play a central role in the observed catalysis.[19,20]

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Conclusion