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IBX-I2 Redox Couple for Facile Generation of IOH and I+: Expedient Protocol for Iodohydroxylation of Olefins and Iodination of Aromatics

Jarugu Narasimha Moorthy*, Kalyan Senapati and Sarvesh Kumar

*Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India, Email: moorthyiitk.ac.in

J. N. Moorthy, K. Senapati, S. Kumar, J. Org. Chem., 2009, 74, 6287-6290.

DOI: 10.1021/jo9007892 (free Supporting Information)



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Abstract

The reduction of IBX to IBA in the presence of molecular iodine in DMSO generates hypoiodous acid (IOH), which reacts with various olefins as well as α,β-unsaturated ketones leading to their respective iodohydrins with anti stereochemistry. The same redox chemistry in acetonitrile containing TFA produces iodonium ions for facile iodination of aromatic compounds.

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Key Words

Iodohydrins, IBX, Iodine


ID: J42-Y2009-2510