Convenient Entry to 18 F-Labeled Amines through the Staudinger Reduction
Research output: Contribution to journal › Journal article › Research › peer-review
Standard
Convenient Entry to 18 F-Labeled Amines through the Staudinger Reduction. / Stéen, E. Johanna L.; Shalgunov, Vladimir; Denk, Christoph; Mikula, Hannes; Kjær, Andreas; Kristensen, Jesper L.; Herth, Matthias M.
In: European Journal of Organic Chemistry, Vol. 2019, No. 8, 2019, p. 1722-1725.Research output: Contribution to journal › Journal article › Research › peer-review
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
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
Y1 - 2019
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
U2 - 10.1002/ejoc.201801457
DO - 10.1002/ejoc.201801457
M3 - Journal article
C2 - 31007573
AN - SCOPUS:85060555182
VL - 2019
SP - 1722
EP - 1725
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 8
ER -
ID: 214298045