Organic solvent accounts for approximately 50% of hazardous waste generated in the pharmaceutical industry. This reality underscores the necessity of finding alternatives to organic solvent as reaction media. Water is an excellent alternative, as it is abundant, non-toxic, and non-hazardous. Unfortunately, water is often unsuitable because many organic reactants and reagents are water-insoluble. Aqueous micellar solutions can help mitigate the insolubility challenges, as water-insoluble starting materials and reagents are entropically driven into the hydrophobic micelle interior, which can facilitate organic reactions. Micelles have not only been shown to catalyze organic reactions, but often do so more efficiently, with fewer side-products, at ambient temperatures. We are designing and synthesizing novel surfactants which self-aggregate into micelles capable of reversibly immobilizing starting materials or catalysts within the micelle. We report progress on the synthesis of an alkene-terminating steroidal-PEG surfactant synthesized from lithocholic acid in five steps. This synthesis was accomplished through an oxidation-decarboxylation pathway followed by PEG headgroup installation through DCC coupling.<br/>

Surfactants with reversible linkers for micelle-facilitated organic synthesis

253rd National Meeting (2017)

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