Mild and Selective Organocatalytic Iodination of Activated Aromatic 
Compounds

Gergely Jakab; Abolfazl Hosseini; Heike Hausmann; Peter R. Schreiner

doi:10.1055/s-0033-1338468

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(12): 1635-1640
DOI: 10.1055/s-0033-1338468

special topic

Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds

Gergely Jakab

Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany Fax: +49(641)9934309 eMail: prs@uni-giessen.de

,

Abolfazl Hosseini

Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany Fax: +49(641)9934309 eMail: prs@uni-giessen.de

,

Heike Hausmann

Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany Fax: +49(641)9934309 eMail: prs@uni-giessen.de

,

Peter R. Schreiner*

Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany Fax: +49(641)9934309 eMail: prs@uni-giessen.de

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Abstract

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Abstract

We describe an organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile. The protocol 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. NMR kinetic investigations conducted in THF-d ₈indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction.

Key words

catalysis - electrophilic aromatic substitution - halogenation - iodine - thiourea

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Referenzen

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