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18 F‐Radiolabeling of Aromatic Compounds Using Triarylsulfonium Salts
Author(s) -
Mu Linjing,
Fischer Cindy R.,
Holland Jason P.,
Becaud Jessica,
Schubiger P. August,
Schibli Roger,
Ametamey Simon M.,
Graham Keith,
Stellfeld Timo,
Dinkelborg Ludger M.,
Lehmann Lutz
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101730
Subject(s) - chemistry , sulfonium , substituent , aryl , yield (engineering) , halogen , nucleophile , nucleophilic substitution , nucleophilic aromatic substitution , medicinal chemistry , electrophilic aromatic substitution , aromaticity , palladium , catalysis , organic chemistry , molecule , alkyl , salt (chemistry) , materials science , metallurgy
A new method for the 18 F‐radiolabeling of aromatic compounds based on the aromatic nucleophilic substitution (S N Ar) reaction using triarylsulfonium salts has been developed. Experiments and DFT calculations indicated that sulfonium ions have the potential to be optimized for labeling nonactivated and deactivated aryl rings that have Hammett σ P substituent constants greater than –0.170. This method is applicable to a range of halogen‐substituted aryl systems including nonactivated and deactivated aryl rings. In particular, the high radiochemical yield of [ 18 F]‐4‐fluoroiodobenzene from precursor 1a represents a ready source of compound 1b for subsequent use in palladium‐catalyzed C–H activation/C–C bond‐forming reactions.