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Dess-Martin Oxidation
Dess-Martin oxidation is a mild synthetic method used to convert primary and secondary alcohols to aldehydes and ketones respectively. The principle compound used for this oxidation is Dess-Martin periodinane (DMP), which can be prepared by two-step synthesis from 2-iodobenzoic acid. Dess-Martin oxidation has several advantages over classic Cr(VI)-based oxidation methods including mild conditions, expanded substrate tolerance, reduced environmental impact, and easy handling and workup. Dess-Martin Oxidation is widely used in organic synthesis, including late-stage total synthesis due to the mild nature of the conditions.
- Reagents:
- Dess-Martin periodinane
- Reactants:
- Alcohols
- Products:
- Aldehydes, Ketones
- Scheme:
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- 1) A Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial®, and Evaluation of Their Olfactory Activity
- 2) Studies on the Himbert Intramolecular Arene/Allene Diels–Alder Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon Tethers
- Original literature:
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- Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
- Review literature:
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- Hypervalent Iodine Reagents for the Oxidation of Alcohols and Their Application to Complex Molecule Synthesis
