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Convenient Entry to 18 F‐Labeled Amines through the Staudinger Reduction
Author(s) -
Stéen E. Johanna L.,
Shalgunov Vladimir,
Denk Christoph,
Mikula Hannes,
Kjær Andreas,
Kristensen Jesper L.,
Herth Matthias M.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801457
Subject(s) - synthon , chemistry , combinatorial chemistry , staudinger reaction , flexibility (engineering) , pet imaging , organic chemistry , positron emission tomography , medicine , statistics , mathematics , radiology
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.