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Wiley, Angewandte Chemie International Edition, 2(63), 2023

DOI: 10.1002/anie.202316365

Wiley, Angewandte Chemie, 2(136), 2023

DOI: 10.1002/ange.202316365

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Zinc‐Mediated Radiosynthesis of Unprotected Fluorine‐18 Labelled α‐Tertiary Amides

Journal article published in 2023 by Jay S. Wright ORCID, Richard Ma, E. William Webb ORCID, Wade P. Winton ORCID, Jenelle Stauff, Kevin Cheng ORCID, Allen F. Brooks ORCID, Melanie S. Sanford ORCID, Peter J. H. Scott ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

AbstractThis report describes the development of a Zn(OTf)2‐mediated method for converting α‐tertiary haloamides to the corresponding fluorine‐18 labelled α‐tertiary fluoroamides with no‐carrier‐added [18F]tetramethylammonium fluoride. 1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene is an essential additive for achieving high radiochemical conversion. Under the optimised conditions, radiofluorination proceeds at sterically hindered tertiary sites in high radiochemical conversions, yields, and purities. This method has been successfully automated and applied to access >200 mCi (>7.4 GBq) of several model radiofluorides. Mechanistic studies led to the development of a new, nucleophilic C−H radiofluorination process using N‐sulphonyloxyamide substrates.