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Issue 44, 2017
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IF5 affects the final stage of the Cl–F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

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Abstract

A difficult chlorine–fluorine (Cl–F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C–S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.

Graphical abstract: IF5 affects the final stage of the Cl–F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

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Publication details

The article was received on 11 Apr 2017, accepted on 09 May 2017 and first published on 09 May 2017


Article type: Communication
DOI: 10.1039/C7CC02802D
Citation: Chem. Commun., 2017,53, 5997-6000
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    IF5 affects the final stage of the Cl–F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

    B. Cui, M. Kosobokov, K. Matsuzaki, E. Tokunaga and N. Shibata, Chem. Commun., 2017, 53, 5997
    DOI: 10.1039/C7CC02802D

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