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A general copper-mediated nucleophilic18F fluorination of arenes

Tredwell, Matthew, Preshlock, Sean M., Taylor, Nicholas J., Gruber, Stefan, Huiban, Mickael, Passchier, Jan, Mercier, Joel, Genicot, Christophe and Gouverneur, Veronique 2014. A general copper-mediated nucleophilic18F fluorination of arenes. Angewandte Chemie International Edition 53 (30) , pp. 7751-7755. 10.1002/anie.201404436

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Abstract

Molecules labeled with fluorine‐18 are used as radiotracers for positron emission tomography. An important challenge is the labeling of arenes not amenable to aromatic nucleophilic substitution (SNAr) with [18F]F−. In the ideal case, the 18F fluorination of these substrates would be performed through reaction of [18F]KF with shelf‐stable readily available precursors using a broadly applicable method suitable for automation. Herein, we describe the realization of these requirements with the production of 18F arenes from pinacol‐derived aryl boronic esters (arylBPin) upon treatment with [18F]KF/K222 and [Cu(OTf)2(py)4] (OTf=trifluoromethanesulfonate, py=pyridine). This method tolerates electron‐poor and electron‐rich arenes and various functional groups, and allows access to 6‐[18F]fluoro‐L‐DOPA, 6‐[18F]fluoro‐m‐tyrosine, and the translocator protein (TSPO) PET ligand [18F]DAA1106.

Item Type: Article
Status: Published
Schools: Medicine
Publisher: Wiley
ISSN: 1433-7851
Last Modified: 04 Jun 2019 11:00
URI: http://orca.cf.ac.uk/id/eprint/122230

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