Iodination of anilines and phenols with 18-crown-6 supported ICl2−

Hannah W. Mbatia; Olbelina A. Ulloa; Daniel P. Kennedy; Christopher D. Incarvito; Shawn C. Burdette

doi:10.1039/C0OB00926A

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Iodination of anilines and phenols with 18-crown-6 supported ICl₂⁻†

Hannah W. Mbatia,^a Olbelina A. Ulloa,^a Daniel P. Kennedy,^a Christopher D. Incarvito^b and Shawn C. Burdette*^a

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* Corresponding authors

^a Department of Chemistry, University of Connecticut, Storrs, USA
E-mail: shawn.burdette@uconn.edu

^b Department of Chemistry, Yale University, 225 Prospect Street, P. O. Box 208107, New Haven, USA

Abstract

A highly crystalline iodinating reagent, {[K·18-C-6]ICl₂}_n, was synthesized in high yield (93%). The trihalide is supported by an 18-crown-6 macrocycle and forms a coordination polymer in the solid state. This reagent iodinates anilines and phenols efficiently under mild conditions. Controlled mono-iodination with anilines was easily achieved while poly-iodination was observed with phenols.

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Article information

DOI: https://doi.org/10.1039/C0OB00926A
Article type: Paper
Submitted: 24 Oct 2010
Accepted: 25 Jan 2011
First published: 26 Jan 2011

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Org. Biomol. Chem., 2011,9, 2987-2991

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Iodination of anilines and phenols with 18-crown-6 supported ICl₂⁻

H. W. Mbatia, O. A. Ulloa, D. P. Kennedy, C. D. Incarvito and S. C. Burdette, Org. Biomol. Chem., 2011, 9, 2987 DOI: 10.1039/C0OB00926A

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Organic & Biomolecular Chemistry