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Geminal difluorination of alpha,alpha '-disubstituted styrenes using fluoro-benziodoxole reagent. Migration aptitude of the alpha-substituents
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 22017 (English)In: Journal of fluorine chemistry, ISSN 0022-1139, E-ISSN 1873-3328, Vol. 203, p. 104-109Article in journal (Refereed) Published
Abstract [en]

alpha,alpha'-Disubstituted styrenes undergo a difluorination-rearrangement reaction with fluoro-benzoiodoxole reagent 1. The reaction is catalyzed by Pd(MeCN)(4)(BF4)(2) and Cu(MeCN)(4)PF6. We have studied the rearrangement of alpha,alpha'-diaryl substituted styrenes, in which the aryl groups have different electronic character. In the case of a aryl, alpha'-alkyl substituted styrenes, the aryl substituent has a higher migratory aptitude than the alkyl group. We have also extended the reactions to cycloalkyl styrenes, which underwent interesting ring contraction/expansion reactions. The regioselectivity of the migration can be explained on the basis of the formation of a phenonium intermediate.

Place, publisher, year, edition, pages
2017. Vol. 203, p. 104-109
Keywords [en]
Difluorination, Rearrangement, Hypervalent fluoroiodine
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-152658DOI: 10.1016/j.jfluchem.2017.07.006ISI: 000418727100010OAI: oai:DiVA.org:su-152658DiVA, id: diva2:1182193
Available from: 2018-02-12 Created: 2018-02-12 Last updated: 2018-02-12Bibliographically approved

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Szabó, Kálmán J.
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