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

The first application of a Sonogashira cross‐coupling reaction in ¹⁸F 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 4‐¹⁸F]fluoroiodobenzene. 4,4′‐Diiododiaryliodonium salts were used as precursors for the synthesis of 4‐¹⁸F]fluoroiodobenzene, enabling the convenient access to 4‐¹⁸F]fluoroiodobenzene in 13–70% yield using conventional heating or microwave activation. The Sonogashira cross‐coupling of 4‐¹⁸F]fluoroiodobenzene with terminal alkynes gave the corresponding 4‐¹⁸F]fluorophenylethynyl‐substituted compounds ¹⁸F]‐9 , ¹⁸F]‐10 and ¹⁸F]‐13 in yields up to 88% within 20 min of starting from 4‐¹⁸F]fluoroiodobenzene. Copyright © 2003 John Wiley & Sons, Ltd.