2‐Benzothiazolyl‐N‐(arenesulfonyl)‐sulfinimidoyl Fluorides.

Pashinnik, V. E.; Guzyr, Alexander I.; Borovikov, Alexei V.; Shermolovich, Yu. G.

doi:10.1002/chin.200547126

Cited by 1 publication

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“…There are no reports of utilizing the Umemoto method to synthesize SF 4 Cl‐ or SF 5 ‐substituted heterocycles, although two papers from Shermolovich et al. described the preparation of SF 3 ‐benzothiazole,8a and 2‐pyridyl, 1‐oxo‐2‐pyridyl, and 2‐pyrimidinylsulfur trifluorides8b using the KF/Cl 2 /MeCN conditions. As arylsulfur trifluorides have been shown to be intermediates during the formation of SF 4 Cl‐substituted aryl compounds,2 it was logical to investigate the same route to prepare pyridyl‐SF 4 Cl compounds as precursors to the corresponding SF 5 ‐substituted pyridines.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

Kanishchev

Dolbier

2014

Angew Chem Int Ed

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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.

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Section: Methodsmentioning

confidence: 99%