DessMartinPeriodinane

Dess–Martin periodinane (DMP) is a hypervalent iodine(V) oxidation reagent used in organic synthesis to convert alcohols to carbonyl compounds under mild, neutral conditions. It is particularly valued for its ability to oxidize primary alcohols to aldehydes and secondary alcohols to ketones with high chemoselectivity and minimal overoxidation.

DMP is derived from iodobenzoate chemistry and is typically available as a solid or as a solution in dichloromethane. It is a moisture- and air-sensitive reagent that should be stored in a dry environment. In practice, it is used in small excess relative to the substrate and is often employed at or near room temperature in common organic solvents such as dichloromethane or acetonitrile.

Typical reaction conditions involve using about 0.5–1.5 equivalents of Dess–Martin periodinane, at 0 to 25 °C, with the reaction generally completing within minutes to a few hours. Workup often includes quenching with a reducing agent such as sodium sulfite or aqueous sodium bicarbonate, followed by standard extraction and purification. The primary byproduct is derived from the oxidized iodine-containing fragment, such as 2-iodobenzoic acid derivatives, which can be removed by chromatography.

DMP is considered milder and more selective than some alternative oxidants, such as IBX, and is widely used in complex molecule synthesis, including natural products and carbohydrate chemistry. It is particularly favored when sensitive functional groups must be preserved. Safety considerations include handling as an oxidizing agent and avoiding exposure to moisture and incompatibly reactive substrates.