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J Org Chem. 2009 Aug 21;74(16):6287-90. doi: 10.1021/jo9007892.

IBX-I2 redox couple for facile generation of IOH and I+: expedient protocol for iodohydroxylation of olefins and iodination of aromatics.

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  • 1Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India. moorthy@iitk.ac.in

Abstract

IBX is readily reduced to IBA in the presence of molecular iodine in DMSO to generate hypoiodous acid (IOH), which reacts with a variety of olefins as well as alpha,beta-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 a variety of aromatic compounds in respectable isolated yields.

PMID:
20560572
[PubMed]
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