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Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

ABSTRACT: A general method for the synthesis of [(18) F]difluoromethylarenes from [(18) F]fluoride for radiopharmaceutical discovery is reported. The method is practical, operationally simple, tolerates a wide scope of functional groups, and enables the labeling of a variety of arenes and heteroarenes with radiochemical yields (RCYs, not decay-corrected) from 10 to 60?%. The (18) F-fluorination precursors are readily prepared from aryl chlorides, bromides, iodides, and triflates. Seven (18) F-difluoromethylarene drug analogues and radiopharmaceuticals including Claritin, fluoxetine (Prozac), and [(18) F]DAA1106 were synthesized to show the potential of the method for applications in PET radiopharmaceutical design.

SUBMITTER: Shi H

PROVIDER: S-EPMC5189681 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

Shi Hang H Braun Augustin A Wang Lu L Liang Steven H SH Vasdev Neil N Ritter Tobias T

Angewandte Chemie (International ed. in English) 20160805 36

A general method for the synthesis of [(18) F]difluoromethylarenes from [(18) F]fluoride for radiopharmaceutical discovery is reported. The method is practical, operationally simple, tolerates a wide scope of functional groups, and enables the labeling of a variety of arenes and heteroarenes with radiochemical yields (RCYs, not decay-corrected) from 10 to 60 %. The (18) F-fluorination precursors are readily prepared from aryl chlorides, bromides, iodides, and triflates. Seven (18) F-difluorometh ...[more]

PMID: 27491349

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