Iodination of Benzylanilines with Potassium Dichloroiodate

Iodination of Benzylanilines with Potassium Dichloroiodate

Mota, George J. M.; Garden, Simon J.

Abstract:

Iodinated organic compounds are widely used in organic synthesis as electrophilic agents for cross-coupling reactions that result in carbon-carbon and carbon-heteroatom bond formation. In this context we are interested in the preparation of ortho-iodoaniline derivatives and we have previously made use of an aqueous solution of potassium dichloroiodate (KICl2) for the iodination of some (hetero-) aromatic systems. The iodination of activated aromatic compounds (such as anilines) readily leads to a mixture of mono-, di- or even tri- iodo products. For example the reaction of p-toluidine with 1.1 equivalents of KICl2 resulted in the obtention of 20% substrate, 60% mono-iodo- and 20% diiodo- p-toluidine. The poor selectivity and a literature precedent for mono-iodination of N-alkylanilines prompted us to investigate the iodination of N-benzylanilines.

Iodinated organic compounds are widely used in organic synthesis as electrophilic agents for cross-coupling reactions that result in carbon-carbon and carbon-heteroatom bond formation. In this context we are interested in the preparation of ortho-iodoaniline derivatives and we have previously made use of an aqueous solution of potassium dichloroiodate (KICl2) for the iodination of some (hetero-) aromatic systems. The iodination of activated aromatic compounds (such as anilines) readily leads to a mixture of mono-, di- or even tri- iodo products. For example the reaction of p-toluidine with 1.1 equivalents of KICl2 resulted in the obtention of 20% substrate, 60% mono-iodo- and 20% diiodo- p-toluidine. The poor selectivity and a literature precedent for mono-iodination of N-alkylanilines prompted us to investigate the iodination of N-benzylanilines.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201382021737

Referências bibliográficas

• [1] 1 a) Evano, G., Blanchard, N., Toumi, M. Chem. Rev. 2008, 108, 3054. b) Buchwald, S.L. Acc. Chem. Res., 2008, 41, 1439. c) Alberico, D., Scott, M.E., Lautens, M. Chem. Rev. 2007, 107, 174.
• [2] 2 Garden, S.J., Torres, J.C., Melo, S.C.S., Lima, A.S., Pinto, A.C., Lima, E.L.S. Tetrahedron Lett. 2001, 42, 2089.
• [3] 3 Shen, H. Vollhardt, K.P.C. Synlett, 2012, 23, 208.

Como citar:

Mota, George J. M.; Garden, Simon J.; "Iodination of Benzylanilines with Potassium Dichloroiodate", p-56-56. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201382021737