Kornblum oxidation uses DMSO to convert suitable alkyl electrophiles into aldehydes or ketones. DMSO participates in the reaction, so it must be considered as a reagent as well as any role it has as the medium.
From alkyl electrophile to carbonyl
The transformation proceeds through an alkoxysulfonium intermediate, followed by base-assisted formation of the carbonyl product. Suitable primary substrates can give aldehydes; suitable secondary substrates can give ketones.
Substrate structure and leaving group determine whether the reaction is useful. Substitution, elimination or decomposition may compete. A statin-intermediate patent includes a Kornblum oxidation option for preparing an aldehyde, illustrating a route-specific application.
Account for reaction and work-up
Measure conversion, carbonyl-product purity and competing products. Include chemically consumed DMSO and sulfur-containing by-products in material balance and separation planning.
The water limit and assay requirement should be based on the actual substrate and procedure. Evaluate solvent removal and recovery together with product isolation. Operating temperature and base selection require assessment of the complete mixture.
For procurement, share the established DMSO specification and expected consumption with YUJI.
Technical references
Further reading: DMSO in Swern Oxidation; DMSO in Parikh–Doering Oxidation.