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Synthesis 2013; 45(12): 1635-1640
DOI: 10.1055/s-0033-1338468
DOI: 10.1055/s-0033-1338468
special topic
Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds
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Publication History
Received: 23 February 2013
Accepted: 17 March 2013
Publication Date:
25 April 2013 (online)
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.
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