Cascade iodination–fluorination synthesis of 2-fluorothiophene and 5-fluoro-2-thienyliodonium salts

The first synthesis of fluorine-containing 2-thienyliodonium salts was accomplished using cascade iodination–fluorination. According to this methodology, thiophene is first converted to bis(2-thienyl)iodonium hexafluorophosphate using an electrophilic iodination reaction. Upon heating with potassium...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2009-05, Vol.130 (5), p.501-504
Main Authors: Onys’ko, Petro P., Kim, Tetyana V., Kiseleva, Olena I., Rassukana, Yuliya V., Gakh, Andrei A.
Format: Article
Language:English
Subjects:
Fluorination
Iodination
Iodonium salts
Thiophene
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Summary:The first synthesis of fluorine-containing 2-thienyliodonium salts was accomplished using cascade iodination–fluorination. According to this methodology, thiophene is first converted to bis(2-thienyl)iodonium hexafluorophosphate using an electrophilic iodination reaction. Upon heating with potassium fluoride, this salt undergoes regioselective fluorination producing 2-fluorothiophene. 2-Fluorothiophene is then iodinated again to yield fluorothienyliodonium salts. The title method was successfully used for the preparation of 2-fluorothiophene and corresponding iodonium salts. The best results were achieved using thermolysis of hexafluorophosphates in the presence of KF.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2009.02.001