Synthesis and Derivatization of 1,1‐[18F]Difluorinated Alkenes

A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) of 1 GBq μmol−1. The transforma...

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Published inAngewandte Chemie International Edition Vol. 58; no. 2; pp. 472 - 476
Main Authors Frost, Aileen B., Brambilla, Marta, Exner, Rüdiger M., Tredwell, Matthew
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.01.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkenes
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Fluorides
Fluorination
Fluorine
fluorine-18
Functional groups
Physical Sciences
positron emission tomography
Radiochemistry
Science & Technology
DRUG
DESIGN
ARENES
fluorination
F-18
IODIDES
fluorine-18
POSITRON-EMISSION-TOMOGRAPHY
RADIOSYNTHESIS
ARYL
INHIBITORS
positron emission tomography
BRAIN
fluorine
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Abstract A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) 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‐[18F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine‐18. 18F‐fluorinated alkenes are excellent building blocks and participate in a number of post‐labeling transformations to access a range of 18F‐perfluorinated functional groups that have never before been radiolabeled with non‐carrier‐added [18F]fluoride. This method considerably expands the range of 18F‐motifs accessible to radiochemists. Some like it hot: A general method for the radiochemical synthesis of 1,1‐[18F]difluoroalkenes from fluoroalkenyl(aryl)iodonium triflates and [18F]fluoride is reported. The 18F‐fluorination reaction is highly regioselective, giving radiochemical purities (RCP) of up to 77 %. The resultant geminal‐difluoroalkenes are versatile 18F‐building blocks, which allow for the first radiochemical syntheses of a range of 18F‐perfluorinated motifs.
AbstractList A general method for the synthesis of 1,1-[F-18]difluorinated alkenes from [F-18]fluoride is reported. This transformation is highly regioselective giving the desired F-18-fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (A(m)) of 1 GBq mu mol(-1). The transformations are operationally simple to perform and were readily translated onto a commercial automated synthesis unit. The resultant 1,1-[F-18]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine-18. F-18-fluorinated alkenes are excellent building blocks and participate in a number of post-labeling transformations to access a range of F-18-perfluorinated functional groups that have never before been radiolabeled with non-carrier-added [F-18]fluoride. This method considerably expands the range of F-18-motifs accessible to radiochemists.
A general method for the synthesis of 1,1-[ F]difluorinated alkenes from [ F]fluoride is reported. This transformation is highly regioselective giving the desired F-fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (A ) of 1 GBq μmol . The transformations are operationally simple to perform and were readily translated onto a commercial automated synthesis unit. The resultant 1,1-[ F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine-18. F-fluorinated alkenes are excellent building blocks and participate in a number of post-labeling transformations to access a range of F-perfluorinated functional groups that have never before been radiolabeled with non-carrier-added [ F]fluoride. This method considerably expands the range of F-motifs accessible to radiochemists.
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.
A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) 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‐[18F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine‐18. 18F‐fluorinated alkenes are excellent building blocks and participate in a number of post‐labeling transformations to access a range of 18F‐perfluorinated functional groups that have never before been radiolabeled with non‐carrier‐added [18F]fluoride. This method considerably expands the range of 18F‐motifs accessible to radiochemists. Some like it hot: A general method for the radiochemical synthesis of 1,1‐[18F]difluoroalkenes from fluoroalkenyl(aryl)iodonium triflates and [18F]fluoride is reported. The 18F‐fluorination reaction is highly regioselective, giving radiochemical purities (RCP) of up to 77 %. The resultant geminal‐difluoroalkenes are versatile 18F‐building blocks, which allow for the first radiochemical syntheses of a range of 18F‐perfluorinated motifs.
A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F‐fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) 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‐[18F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine‐18. 18F‐fluorinated alkenes are excellent building blocks and participate in a number of post‐labeling transformations to access a range of 18F‐perfluorinated functional groups that have never before been radiolabeled with non‐carrier‐added [18F]fluoride. This method considerably expands the range of 18F‐motifs accessible to radiochemists.
Author Frost, Aileen B.
Tredwell, Matthew
Brambilla, Marta
Exner, Rüdiger M.
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Issue 2
Keywords DRUG
DESIGN
ARENES
fluorination
F-18
IODIDES
fluorine-18
POSITRON-EMISSION-TOMOGRAPHY
RADIOSYNTHESIS
ARYL
INHIBITORS
positron emission tomography
BRAIN
fluorine
Language English
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Snippet A general method for the synthesis of 1,1‐[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the...
A general method for the synthesis of 1,1-[F-18]difluorinated alkenes from [F-18]fluoride is reported. This transformation is highly regioselective giving the...
A general method for the synthesis of 1,1-[ F]difluorinated alkenes from [ F]fluoride is reported. This transformation is highly regioselective giving the...
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...
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SubjectTerms Alkenes
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Fluorides
Fluorination
Fluorine
fluorine-18
Functional groups
Physical Sciences
positron emission tomography
Radiochemistry
Science & Technology
Title Synthesis and Derivatization of 1,1‐[18F]Difluorinated Alkenes
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201810413
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https://www.ncbi.nlm.nih.gov/pubmed/30452114
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