Hypervalent phenyl-[small lambda]3-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers

Exposure of 3-phenylpropyl ethers to an activated iodosylbenzene monomer[middle dot]18-crown-6 complex [PhI(OH)BF4[middle dot]18C6] in the presence of BF3-Et2O and water results in the para-selective monofluorination of benzene ring via neighboring alkoxy group participation and directly affords 3-(...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (12), p.3410-3412
Main Authors: Saito, Motomichi, Miyamoto, Kazunori, Ochiai, Masahito
Format: Article
Language:English
Subjects:
Activated
Benzene
Ethers
Fluorination
Rings (mathematics)
Online Access:Get full text
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Summary:Exposure of 3-phenylpropyl ethers to an activated iodosylbenzene monomer[middle dot]18-crown-6 complex [PhI(OH)BF4[middle dot]18C6] in the presence of BF3-Et2O and water results in the para-selective monofluorination of benzene ring via neighboring alkoxy group participation and directly affords 3-(4-fluorophenyl)propyl ethers regioselectively in good yields.
ISSN:1359-7345
DOI:10.1039/C1CC10215J