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Iodine(V) Reagents in Organic Synthesis. Part 4. o-Iodoxybenzoic Acid as a Chemospecific Tool for Single Electron Transfer-Based Oxidation Processes

K. C. Nicolaou,* T. Montagnon, P. S. Baran and Y.-L. Zhong

*The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Rd., La Jolla, California 92037, Email: kcnscripps.edu

K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245-2258.

DOI: 10.1021/ja012127+ (free Supporting Information)


Abstract

o-Iodoxybenzoic acid (IBX) was found to be highly effective in oxidations adjacent to carbonyl and benzylic functionalities to form either α,β-unsaturated carbonyl compounds or conjugated aromatic carbonyl systems. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates.

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Key Words

o-Iodoxybenzoic acid, hypervalent iodine reagents, enones, aldehydes, ketones


ID: J48-Y2002-1080