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

Narasimha Moorthy, Jarugu ; Senapati, Kalyan ; Kumar, Sarvesh (2009) IBX-I2 redox couple for facile generation of IOH and I+: expedient protocol for iodohydroxylation of olefins and iodination of aromatics Joural of Organic Chemistry, 74 (16). pp. 6287-6290. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo9007892

Related URL: http://dx.doi.org/10.1021/jo9007892

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 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 a variety of aromatic compounds in respectable isolated yields.

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Deposited On:10 Sep 2011 11:41
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