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Dess-Martin Oxidation

Dess-Martin oxidation mechanism   Named Reactions in Organic Synthesis
Reaction category:
Oxidation

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During the 1980s hypervalent iodine reagents were developed as selective, mild and environmentally friendly oxidizing agents for organic synthesis. Perhaps the most important group of these reagents are periodinanes (derivatives of pentacoordinate iodine (V)), and the most well-known of these include the reagents 2-iodoxybenzoic acid (IBX) and Dess–Martin periodinane (DMP). Whilst IBX had been known since 1893, its insolubility in most organic solvents inhibited its use in organic synthesis. However, in 1983 D.B. Dess and J.C. Martin described the preparation of DMP, a far more soluble alternative. Since this discovery, DMP has become the reagent of choice for the oxidation of alcohols to their corresponding carbonyl compounds, and oxidations using DMP are known as Dess–Martin oxidations.

In the total synthesis of ustiloxin D, a highly potent inhibitor of microtubule assembly, M.M. Joullié and co-workers utilised DMP to convert a macrocyclic primary alcohol into its corresponding aldehyde.

Dess-Martin oxidation mechanism:

mechanism of Dess-Martin oxidation

 
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Some relevant Alfa Aesar products for the Dess-Martin oxidation:

2-Iodobenzoic acid, 98+%
Dess-Martin periodinane
Potassium bromate, 99%
Oxone®, monopersulfate

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