High-throughput purification of solution-phase periodinane mediated oxidation reactions utilizing a novel thiosulfate resin

Article abstract of DOI:10.1016/S0040-4020(99)00342-7

A simple and efficient methodology for sequestering byproducts and excess starting reagent from the solution-phase Dess-Martin and Grieco-Dess- Martin periodinane mediated oxidation of primary or secondary alcohols to aldehydes or ketones is described. The periodinane oxidations are carried out under mild conditions followed by treatment with a novel thiosulfate resin which reduces any remaining I(V) and I(III) periodinane species to an I(I) species. Quantitative removal of the I(I) species from the solution is achieved by using a base functionalized resin followed by filtration and evaporation to afford highly pure aldehyde or ketone products. Utilization of this sequestration methodology for periodinane mediated oxidations allows for the high-throughput purification and work-up of parallel reaction chambers and is highly amenable to automation procedures.