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Synthesis and Derivatization of 1,1‐[ 18 F]Difluorinated Alkenes
Author(s) -
Frost Aileen B.,
Brambilla Marta,
Exner Rüdiger M.,
Tredwell Matthew
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810413
Subject(s) - alkene , derivatization , chemistry , fluorine , regioselectivity , fluoride , molecule , combinatorial chemistry , medicinal chemistry , organic chemistry , inorganic chemistry , high performance liquid chromatography , catalysis
A general method for the synthesis of 1,1‐[ 18 F]difluorinated alkenes from [ 18 F]fluoride is reported. This transformation is highly regioselective giving the desired 18 F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (A m ) of 1 GBq μmol −1 . The transformations are operationally simple to perform and were readily translated onto a commercial automated synthesis unit. The resultant 1,1‐[ 18 F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine‐18. 18 F‐fluorinated alkenes are excellent building blocks and participate in a number of post‐labeling transformations to access a range of 18 F‐perfluorinated functional groups that have never before been radiolabeled with non‐carrier‐added [ 18 F]fluoride. This method considerably expands the range of 18 F‐motifs accessible to radiochemists.