Organic solvents are routinely used in both academia and industry, and yet represent ≥80% of the organic waste produced by the chemical industry worldwide.1 Moreover, despite the fact that many are recognized as carcinogens, reproductive hazards or neurotoxins, and are highly flammable, nonetheless the vast majority of reactions in organic chemistry are still conducted in organic solvents. Making the “switch”2 to water as a reaction rather than a workup medium, thus following Nature’s lead, can be challenging, as most starting materials are insoluble, forcing reactions to be conducted at higher temperatures that can lead to undesirable by-products. The introduction of benign-by-design surfactants such as TPGS-750-M3 or “Nok”4 that form nanomicelles in water, help the dissolution of organic partners within their cores. Due to high concentrations of reactants in these nanoreactors associated with the hydrophobic effect, reactions can be performed under mild and safe conditions. Associated E Factors are very low, especially as the reaction media can be recycled many times. The latest applications developed in our group will be discussed with an emphasis on ppm level metal-catalyzed processes, peptide synthesis, and the judicious use of a minimal amount of co-solvent as a ‘trick’ that enables use of this technology for industrial applications.

Principle 3. Towards organic chemistry without organic solvents: The case for use of designer surfactants for safer organic reactions

255th National Meeting (2018)

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