Affiliation:
1. Molecular Imaging Branch National Institute of Mental Health National Institutes of Health 10 Center Drive Bethesda MD 20892–1003 USA
2. Gordon Center for Medical Imaging Department of Radiology Massachusetts General Hospital and Harvard Medical School Boston, MA <02114-1107> postcode missing<02114-1107> USA
Abstract
AbstractEfficient methods for labeling aryl trifluoromethyl groups to provide novel radiotracers for use in biomedical research with positron emission tomography (PET) are keenly sought. We report a broad‐scope method for labeling trifluoromethylarenes with either carbon‐11 (t1/2=20.4 min) or fluorine‐18 (t1/2=109.8 min) from readily accessible aryl(mesityl)iodonium salts. In this method, the aryl(mesityl)iodonium salt is treated rapidly with no‐carrier‐added [11C]CuCF3 or [18F]CuCF3. The mesityl group acts as a spectator allowing radiolabeled trifluoromethylarenes to be obtained with very high chemoselectivity. Radiochemical yields from aryl(mesityl)iodonium salts bearing either electron‐donating or electron‐withdrawing groups at meta‐ or para‐ position are good to excellent (67–96 %). Ortho‐substituted and otherwise sterically hindered trifluoromethylarenes still give good yields (15–34 %). Substituted heteroaryl(mesityl)iodonium salts are also viable substrates. The broad scope of this method was further exemplified by labeling a previously inaccessible target, [11C]p‐trifluoromethylphenyl boronic acid, as a potentially useful labeling synthon. In addition, fluoxetine, leflunomide, and 3‐trifluoromethyl‐4‐aminopyridine, as examples of small drug‐like molecules and candidate PET radioligands, were successfully labeled in high yields (69–81 %).
Funder
National Institute of Mental Health
National Institute of Biomedical Imaging and Bioengineering
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
7 articles.
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