UC Santa Barbara

The world of modern organic chemistry, a very traditional but unsustainable 200-year-old discipline, relies heavily on the use of environmentally harmful chemicals. From the 12 Principles of Green Chemistry it is evident that waste-generating and toxic organic solvents must be eliminated and replaced by the greenest solvent, recyclable water. New surfactants were developed by the Lipshutz lab which forms nano-micelles in water to serve as organic reaction vessels. Micellar catalysis has been advantageous by enabling a myriad of synthetic organic reactions. Recent advancements utilize enzymes such as lipases for bio-catalytic processes that benefit significantly when run in the presence of these nanomicelles, offering an advantageous and unprecedented “reservoir effect” that minimizes textbook enzymatic inhibition. In addition, the study of substrate promiscuity for lipases that catalyze esterification reactions, focuses on the use of a simple, economical and commercially available additive. The common aqueous micellar reaction medium provides the synergy between chemo- and bio-catalytic processes giving rise to the blossoming field of “chemoenzymatic catalysis” that can now occur sequentially in 1-pot in various permutations and combinations. These cascade reactions abide by many principles of green chemistry such as time- and pot-economy and illustrate the potential of conducting sequential organic transformations including industrial drug development, under ambient condition with low levels of precious metal catalyst loadings. One such example is the synthesis of an anticancer drug, erdafitinib which is achieved in a 3-step, 2-pot sequence under aqueous micellar conditions enabled by a biodegradable surfactant, Savie.