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Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds

Gergely Jakab, Abolfazl Hosseini, Heike Hausmann, Peter R. Schreiner*

*Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany, Email: prsuni-giessen.de

G. Jakab, A. Hosseini, H. Hausmann, P. R. Schreiner, Synthesis, 2013, 45, 1635-1640.

DOI: 10.1055/s-0033-1338468 (free Supporting Information)


Abstract

An organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile is applicable to a number of aromatic substrates with significantly different steric and electronic properties. The iodination is generally highly regioselective and provides high yields of isolated products.

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Key Words

organocatalysis, electrophilic aromatic substitution, iodination, iodine, thiourea, 1,3-diiodo-5,5-dimethylhydantoin


ID: J66-Y2013