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N.C.A. 18F-fluoroalkylation of H-acidic compounds

✍ Scribed by Dirk Block; Heinz Hubert Coenen; Gerhard Stöcklin

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
563 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

The fluoroalkylation of H-acidic compounds in the presence of the aminopolyether 2.2.2./potassium carbonate complex was systematically studied. With acetonitrile as solvent nucleophilic fluorination and subsequent fluoroalkylation can be carried out in a one-pot mode. Using the bifunctional fluoroalkanes 18F(CH2)nX (n = 1-3, X = Br, OMes, OTos) the best n.c.a. labelling yields were obtained with tosylates. Fluoroethylation and fluoropropylation of phenol gave rise to radiochemical yields of 2 90% under optimized conditions within 10 min. The fluoroethyl moiety is the smallest generally applicable fluoroalkylation agent. In a series of H-acidic compounds a strong influence of their pKa value on the fluoroethylation reaction was observed. Besides H-acidic compounds all Lewis bases are principally potential substrates for n.c.a. 18F-fluoroalkylation.

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