In many ways, water is an ideal solvent: it is cheap, abundant, renewable, non-toxic, and non-flammable, making it the prime alternative to the organic solvents used in chemical reactions. Unfortunately, the water insolubility of most organic compounds limits its use as a solvent. Significant progress has been made in micellar catalysis, in which organic reactions take place in the organic medium in the interior of the micelle. We report our progress in creating micelles capable of catalyzing a sequence of reactions analogous to solid-phase synthesis, in which the reactants are tethered to the interior of the micelle through a reversible linker . Specifically, we synthesized a derivative of a currently produced steroidal surfactant, SPGS-550-M. This derivative contains a terminal alkene linked to the D-ring of the steroid in place of the β-sitosterol side-chain present in SPGS-550-M. We hypothesize that this new surfactant, <b>1</b>, when mixed with SPGS-550-M in water, will generate micelles capable of immobilizing alkenyl starting materials through cross-metathesis reactions. Future work will demonstrate the ability of these micelles to facilitate Negishi-type palladium-catalyzed cross-coupling reactions on an immobilized alkyl halide, cleave, and extract the subsequent product. We will also demonstrate the reusability of the micelles and characterize the micelles by DLS, cryo-TEM, and pulse-field gradient NMR.

Surfactants with reversible linkers for micelle-facilitated organic synthesis

251st National Meeting (2016)

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