Journal article

Publication year: 2013

Pages: 1635-1640

Journal: Synthesis: Journal of Synthetic Organic Chemistry

Volume number: 45

Issue number: 12

DOI Link: https://doi.org/10.1055/s-0033-1338468

Publisher: Thieme Publishing / Georg Thieme Verlag

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 ₈ indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction.

Harvard Citation style: Jakab, G., Hosseini, A., Hausmann, H. and Schreiner, P. (2013) Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds, Synthesis: Journal of Synthetic Organic Chemistry, 45(12), pp. 1635-1640. https://doi.org/10.1055/s-0033-1338468

APA Citation style: Jakab, G., Hosseini, A., Hausmann, H., & Schreiner, P. (2013). Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds. Synthesis: Journal of Synthetic Organic Chemistry. 45(12), 1635-1640. https://doi.org/10.1055/s-0033-1338468