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Issue 26, 2014
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Halocarbocyclization versus dihalogenation: substituent directed iodine(iii) catalyzed halogenations

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Abstract

The nucleophilicity of the substituents in iodobenzene pre-catalysts have a huge impact on product selectivity in iodine(III) triggered halogenations, steering the reactivity from solely carbocyclizations towards dihalogenations. Utilizing this catalyst-dependent reactivity a diastereo- and chemoselective dihalogenation method was established allowing the conversion of structurally and electronically diverse unsaturated compounds in excellent yields.

Graphical abstract: Halocarbocyclization versus dihalogenation: substituent directed iodine(iii) catalyzed halogenations

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Supplementary files

Article information


Submitted
30 Dec 2013
Accepted
04 Feb 2014
First published
06 Feb 2014

Chem. Commun., 2014,50, 3435-3438
Article type
Communication
Author version available

Halocarbocyclization versus dihalogenation: substituent directed iodine(III) catalyzed halogenations

M. Stodulski, A. Goetzinger, S. V. Kohlhepp and T. Gulder, Chem. Commun., 2014, 50, 3435
DOI: 10.1039/C3CC49850F

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