Synthesis and characterization of 2-pyridylsulfur pentafluorides.
Current approaches to prepare SF5 -substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5 -functionalized aryl or alkyne reagents or SF5 Cl as a source of the SF5  functional group. Herein we report that excess oxidative fluorination of 2,2'-dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4 Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5 -pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5 -substituted heterocycles.
Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL 32611 (USA).
Oleksandr S
OS
Kanishchev
William R
WR
Dolbier
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry*; D005459:Fluorides / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D010084:Oxidation-Reduction
D004220:Disulfides; C001105:2,2'-dipyridyl disulfide; D015082:2,2'-Dipyridyl; D005459:Fluorides
fluorination; halogen-exchange reactions; heterocycles; oxidation; pentafluorosulfanyl substituents