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Synthesis of 4-[18F]fluoroiodobenzene and its application in sonogashira cross-coupling reactions

✍ Scribed by Frank R. Wüst; Torsten Kniess

Publisher
John Wiley and Sons
Year
2003
Tongue
French
Weight
146 KB
Volume
46
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The first application of a Sonogashira cross‐coupling reaction in ^18^F chemistry has been developed. The reaction was exemplified by the cross‐coupling of terminal alkynes (ethynylcyclopentyl carbinol 6, 17α‐ethynyl‐3,17β‐estradiol 7 and 17α‐ethynyl‐3‐methoxy‐3,17β‐estradiol 8) with 4‐[^18^F]fluoroiodobenzene. 4,4′‐Diiododiaryliodonium salts were used as precursors for the synthesis of 4‐[^18^F]fluoroiodobenzene, enabling the convenient access to 4‐[^18^F]fluoroiodobenzene in 13–70% yield using conventional heating or microwave activation. The Sonogashira cross‐coupling of 4‐[^18^F]fluoroiodobenzene with terminal alkynes gave the corresponding 4‐[^18^F]fluorophenylethynyl‐substituted compounds [^18^F]‐9, [^18^F]‐10 and [^18^F]‐13 in yields up to 88% within 20 min of starting from 4‐[^18^F]fluoroiodobenzene. Copyright © 2003 John Wiley & Sons, Ltd.

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