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

PP Onys'ko, TV Kim, OI Kiseleva, YV Rassukana…

Index: Onys'ko, Petro P.; Kim, Tetyana V.; Kiseleva, Olena I.; Rassukana, Yuliya V.; Gakh, Andrei A. Journal of Fluorine Chemistry, 2009 , vol. 130, # 5 p. 501 - 504

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Citation Number: 10

Abstract

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 ...