Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 203, Issue -, Pages 104-109Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2017.07.006
Keywords
Difluorination; Rearrangement; Hypervalent fluoroiodine
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Funding
- Swedish Research Council (VR)
- Knut och Alice Wallenbergs Foundation
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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.
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