UC Santa Barbara

I. A sustainable method for reductive aminations using shelf-stable bisulfite addition compounds of aldehydes under aqueous micellar catalysis is presented. Using α-picolineborane as a readily available stoichiometric hydride source, we successfully synthesized highly valued compounds, inclusive of those pertinent to the pharmaceutical domain. Moreover, this method allows for straightforward recycling of the aqueous reaction medium, emphasizing its environmental benefits.

II. Under micellar catalysis conditions, an eco-friendly nitro group reduction has been developed using readily accessible Pd/C as a catalyst with a minimal Pd loading of 0.4 mol %. This methodology efficiently facilitates the transformation of a diverse range of nitro compounds into their corresponding amines, yielding notable results. The robustness of this process is further showcased through the one-pot synthesis of specific pharmaceutical intermediates. Notably, both the catalyst and the surfactant have demonstrated consistent recyclability without any decrease in effectiveness.

III. The introduction of nonionic surfactant to aqueous reaction systems with varied IREDs significantly enhances both the reaction rate and the yield of the target amines, with improvements reaching more than 40% in comparison to buffer only. Moreover, these findings underscore the potential of combining chemocatalysis and biocatalysis into a 1-pot sequence under aqueous micellar environments. Multiple 1-pot procedures integrating the use of IREDs with diverse chemo-catalytic methods were shown.

IV. Ketones, both aromatic and heteroaromatic, possessing an α-methine proton, have been demonstrated to undergo deprotonation and subsequent mono-allylation rapidly and exclusively in the absence of any solvent. This process consistently delivers the targeted products with excellent isolated yields. The versatility and applicability of this novel method are further highlighted through its successful application to the synthesis of notable compounds such as MK-7, MK-9, and coenzyme Q9 (CoQ9).