A General Copper‐Mediated Nucleophilic 18F Fluorination of Arenes1. Issue 30 (10th June 2014)

• Record Type: Journal Article
• Authors: Tredwell, Matthew; Preshlock, Sean M.; Taylor, Nicholas J.; Gruber, Stefan; Huiban, Mickael; Passchier, Jan; Mercier, Joël; Génicot, Christophe; Gouverneur, Véronique
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 30(2014)
• Page Start: 7751
• Page End: 7755
• Publication Date: 2014-06-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201404436
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 (S_NAr) 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‐<sc>L</sc>‐DOPA, 6‐[¹⁸F]fluoro‐<italic>m</italic>‐tyrosine, and the translocator protein (TSPO) PET ligand [¹⁸F]DAA1106.</p> </abstract>