Zhou Pan-hon
2015
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Guangzhou Chemical Industry
Abstract
A metal- free synthesis of [2- [( di- tert- butoxycarbonyl)- amino]- 3- methoxy- 3- o- xopropyl- phenyl]-( phenyl) iodonium hexafluorophosphate from the corresponding iodoarene was reported. Trimethylsilyl acetate( TMSOAc) was used to tame the reactive I( III) intermediate formed from oxidation of 2- amino- 3-( 4- iodophenyl)propanoic acid by N- F reagents. The corresponding diacetoxyiodoarene could be obtained without damaging the acid-sensitive Boc protecting groups. The I( III) intermediate could be converted to the corresponding diaryliodonium salts by reacting with benzenetrifluoroboric acid potassium salt and potassium hexaflourophosphate in excellent isolated yield. The iodonium salt was a useful precursor for synthesis of18F- fluorophenalanine,an18F- labled amino acid to be used as a radio tracer for positron emission tomography( PET). The structure of the product was confirmed by1H- NMR,13C-NMR and mass spectroscopy.