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

Chemical Communications : Chem Comm
Benqiang CuiNorio Shibata

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.

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Citations

Oct 9, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yuji SumiiNorio Shibata
Dec 16, 2021·Chemical Communications : Chem Comm·Thanh V Le, Olafs Daugulis

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