IF5 affects the final stage of the Cl-F exchange fluorination in the synthesis of pentafluoro-lambda(6)-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents

A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-lambda(6)-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 clea...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 44; pp. 5997 - 6000
Main Authors Cui, Benqiang, Kosobokov, Mikhail, Matsuzaki, Kohei, Tokunaga, Etsuko, Shibata, Norio
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.06.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
TRIFLUOROMETHYL
SULFIDES
ANALOGS
BIOLOGICAL-ACTIVITY
CHEMISTRY
SALTS
POLYFLUORINATION
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Summary:A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-lambda(6)-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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc02802d