Convenient Entry to 
                        18
                        F-Labeled Amines through the Staudinger Reduction

E. Johanna L. Stéen; Vladimir Shalgunov; Christoph Denk; Hannes Mikula; Andreas Kjær; Jesper L. Kristensen; Matthias M. Herth

doi:10.1002/ejoc.201801457

Convenient Entry to ¹⁸ F-Labeled Amines through the Staudinger Reduction

E. Johanna L. Stéen, Vladimir Shalgunov, Christoph Denk, Hannes Mikula, Andreas Kjær, Jesper L. Kristensen, Matthias M. Herth^*

^*Corresponding author for this work

Cluster for Molecular Imaging

Abstract

Fluorine-18 possesses outstanding decay characteristics for positron emission tomography (PET) imaging. Therefore, it is ideally suited for clinical applications. As such, improved strategies to incorporate fluorine-18 into bioactive molecules are of utmost importance. Indirect ¹⁸ F-labeling with amino-functionalized synthons is a convenient and versatile approach to synthesize a broad variety of PET tracers. Herein, we report a method to convert ¹⁸ F-labeled azides to primary amines by means of the Staudinger reduction. Aliphatic and aromatic ¹⁸ F-labeled azides were converted into the corresponding amines with high conversion yields. The method was easily automated. From a broader perspective, the applied strategy results in two useful synthons from a single precursor and thus increases the flexibility to label diverse chemical scaffolds with minimal synthetic effort.

Original language	English
Journal	European Journal of Organic Chemistry
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201801457
Publication status	Published - 28 Feb 2019

Keywords

Amines
Azides
Fluorine
Radiochemistry
Reduction

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title = "Convenient Entry to 18 F-Labeled Amines through the Staudinger Reduction",

abstract = " Fluorine-18 possesses outstanding decay characteristics for positron emission tomography (PET) imaging. Therefore, it is ideally suited for clinical applications. As such, improved strategies to incorporate fluorine-18 into bioactive molecules are of utmost importance. Indirect 18 F-labeling with amino-functionalized synthons is a convenient and versatile approach to synthesize a broad variety of PET tracers. Herein, we report a method to convert 18 F-labeled azides to primary amines by means of the Staudinger reduction. Aliphatic and aromatic 18 F-labeled azides were converted into the corresponding amines with high conversion yields. The method was easily automated. From a broader perspective, the applied strategy results in two useful synthons from a single precursor and thus increases the flexibility to label diverse chemical scaffolds with minimal synthetic effort. ",

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doi = "10.1002/ejoc.201801457",

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T1 - Convenient Entry to 18 F-Labeled Amines through the Staudinger Reduction

AU - Stéen, E. Johanna L.

AU - Shalgunov, Vladimir

AU - Denk, Christoph

AU - Mikula, Hannes

AU - Kjær, Andreas

AU - Kristensen, Jesper L.

AU - Herth, Matthias M.

PY - 2019/2/28

Y1 - 2019/2/28

N2 - Fluorine-18 possesses outstanding decay characteristics for positron emission tomography (PET) imaging. Therefore, it is ideally suited for clinical applications. As such, improved strategies to incorporate fluorine-18 into bioactive molecules are of utmost importance. Indirect 18 F-labeling with amino-functionalized synthons is a convenient and versatile approach to synthesize a broad variety of PET tracers. Herein, we report a method to convert 18 F-labeled azides to primary amines by means of the Staudinger reduction. Aliphatic and aromatic 18 F-labeled azides were converted into the corresponding amines with high conversion yields. The method was easily automated. From a broader perspective, the applied strategy results in two useful synthons from a single precursor and thus increases the flexibility to label diverse chemical scaffolds with minimal synthetic effort.

AB - Fluorine-18 possesses outstanding decay characteristics for positron emission tomography (PET) imaging. Therefore, it is ideally suited for clinical applications. As such, improved strategies to incorporate fluorine-18 into bioactive molecules are of utmost importance. Indirect 18 F-labeling with amino-functionalized synthons is a convenient and versatile approach to synthesize a broad variety of PET tracers. Herein, we report a method to convert 18 F-labeled azides to primary amines by means of the Staudinger reduction. Aliphatic and aromatic 18 F-labeled azides were converted into the corresponding amines with high conversion yields. The method was easily automated. From a broader perspective, the applied strategy results in two useful synthons from a single precursor and thus increases the flexibility to label diverse chemical scaffolds with minimal synthetic effort.

KW - Amines

KW - Azides

KW - Fluorine

KW - Radiochemistry

KW - Reduction

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U2 - 10.1002/ejoc.201801457

DO - 10.1002/ejoc.201801457

M3 - Journal article

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SN - 1434-193X

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Convenient Entry to ¹⁸ F-Labeled Amines through the Staudinger Reduction

Abstract

Keywords

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