Literature DB >> 20560572

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

Jarugu Narasimha Moorthy1, Kalyan Senapati, Sarvesh Kumar.   

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.

Entities:  

Year:  2009        PMID： 20560572     DOI： 10.1021/jo9007892

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors.

Authors:  Amber D Somoza; Kuan-Han Lee; Yi-Ming Chiang; Berl R Oakley; Clay C C Wang
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

2.  β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Authors:  Jakub Saadi; Hisashi Yamamoto
Journal:  Chemistry       Date:  2013-02-19       Impact factor: 5.236

3.  Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P-(+)-dispegatrine and six other monomeric indole alkaloids.

Authors:  Chitra R Edwankar; Rahul V Edwankar; Ojas A Namjoshi; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

4.  Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes.

Authors:  Igor B Krylov; Stanislav A Paveliev; Mikhail A Syroeshkin; Alexander A Korlyukov; Pavel V Dorovatovskii; Yan V Zubavichus; Gennady I Nikishin; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2018-08-16       Impact factor: 2.883
  4 in total

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