Hypervalent phenyl-λ3-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers

Motomichi Saito; Kazunori Miyamoto; Masahito Ochiai

doi:10.1039/C1CC10215J

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Hypervalent phenyl-λ³-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers†

Motomichi Saito,^a Kazunori Miyamoto*^a and Masahito Ochiai^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan
E-mail: kmiya@ph.tokushima-u.ac.jp
Fax: +81 88-633-9504

Abstract

Exposure of 3-phenylpropyl ethers to an activated iodosylbenzene monomer·18-crown-6 complex [PhI(OH)BF₄·18C6] in the presence of BF₃–Et₂O and water results in the para-selective monofluorination of benzene ringvia neighboring alkoxy group participation and directly affords 3-(4-fluorophenyl)propyl ethers regioselectively in good yields.

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Article information

DOI: https://doi.org/10.1039/C1CC10215J
Article type: Communication
Submitted: 12 Jan 2011
Accepted: 07 Feb 2011
First published: 21 Feb 2011

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Chem. Commun., 2011,47, 3410-3412

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Hypervalent phenyl-λ³-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers

M. Saito, K. Miyamoto and M. Ochiai, Chem. Commun., 2011, 47, 3410 DOI: 10.1039/C1CC10215J

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