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Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes.
Wright, Jay S; Sharninghausen, Liam S; Preshlock, Sean; Brooks, Allen F; Sanford, Melanie S; Scott, Peter J H.
Afiliação
  • Wright JS; Department of Radiology, University of Michigan, Ann Arbor, Michigan 48109, United States.
  • Sharninghausen LS; Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
  • Preshlock S; Department of Radiology, University of Michigan, Ann Arbor, Michigan 48109, United States.
  • Brooks AF; Department of Radiology, University of Michigan, Ann Arbor, Michigan 48109, United States.
  • Sanford MS; Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
  • Scott PJH; Department of Radiology, University of Michigan, Ann Arbor, Michigan 48109, United States.
J Am Chem Soc ; 143(18): 6915-6921, 2021 05 12.
Article em En | MEDLINE | ID: mdl-33914521
ABSTRACT
This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/µmol (19.24 GBq/µmol) molar activity (Am), respectively.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ácidos Borônicos / Cobre / Ésteres / Fluoretos / Compostos de Amônio Quaternário / Irídio Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ácidos Borônicos / Cobre / Ésteres / Fluoretos / Compostos de Amônio Quaternário / Irídio Idioma: En Ano de publicação: 2021 Tipo de documento: Article