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

---

see article for more reactions

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.

see article for more examples

---

---

Key Words

Iodohydrins, IBX, Iodine

---

ID: J42-Y2009-2510