Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [(18)F]fluoride ion rapidly affords no-carrier-added [(18)F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [(18)F]fluoroarenes in just two steps.
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| http://dx.doi.org/10.1021/acs.joc.5b02332 | DOI Listing |
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Division of Nuclear Medicine and Molecular Imaging & Gordon Center for Medical Imaging, Massachusetts General Hospital, 55 Fruit Street, Boston, Massachusetts, 02114, United States of America; Department of Radiology, Harvard Medical School, 55 Fruit Street, Boston, Massachusetts, 02114, United States of America.
Synthesis of non-activated electron-rich and sterically hindered F-arenes remains a major challenge due to limitations of existing radiofluorination methodologies. Herein, we report on our mechanistic investigations of spirocyclic iodonium(III) ylide precursors for arene radiofluorination, including their reactivity, selectivity, and stability with no-carrier-added [F]fluoride. Benchmark calculations at the G2[ECP] level indicate that pseudorotation and reductive elimination at iodine(III) can be modeled well by appropriately selected dispersion-corrected density functional methods.
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Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health , Building 10, Room B3 C346A, 10 Center Drive, Bethesda, Maryland 20892-1003, United States.
Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [(18)F]fluoride ion rapidly affords no-carrier-added [(18)F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [(18)F]fluoroarenes in just two steps.
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Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health, Bethesda, MD 20892-1003, USA.
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Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health, Bethesda, MD 20892, USA.
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