Dess-Martin-Periodinane: Mild Selective Reagent for Oxidation of Alcohols

Dess-Martin-Periodinane is one of the most useful reagents for the reduction of primary and secondary alcohols to aldehydes and ketones. Mild reaction conditions (ambient temperature, no need for acidic or basic additives), high yields, and a superior chemoselectivity for alcohols make it an ideal reagent for the oxidation of complex compounds such as natural products with many other nonhydroxylic functional groups that should be left unchanged. No wonder that the original paper of Dess and Martin (1983) is one of the most cited ever published in Journal of Organic Chemistry!

References:

• Dess, D. B.; Martin, J. C., Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones, J. Org. Chem., (1983) 48, 4155.
• Dess, D. B.; Martin, J. C., A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species, J. Am. Chem. Soc., (1991) 113, 7277.
• Ramachandran, P. V. et al., Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: a novel protocol for the stereoselective synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide, J. Org. Chem., (2004) 69, 6294.
• Zhdankin, V. V. et al., Esters of 2-iodoxybenzoic acid: hypervalent iodine oxidizing reagents with a pseudobenziodoxole structure, J. Org. Chem., (2005) 70, 6484.
• Thongsornkleeb, C.; Danheiser, R.L., A Practical Method for the Synthesis of 2-Alkynylpropenals, J. Org. Chem., (2005) 70, 2364.
• Zhdankin, V. V.; Organoiodine(V) reagents in organic synthesis; J. Org. Chem., (2005) 70, 6484.

Find many more examples on: http://www.synarchive.com/named-reactions/Dess-Martin_Oxidation