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

A simple and efficient methodology for sequestering byproducts and excess s tarting reagent from the solution-phase Dess-Martin and Grieco-Dess-Martin periodinane mediated oxidation of primary or secondary alcohols to aldehyde s 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) speci es. 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 seq uestration methodology for periodinane mediated oxidations allows for the h igh-throughput purification and work-up of parallel reaction chambers and i s highly amenable to automation procedures. (C) 1999 Elsevier Science Ltd. All rights reserved.