title: Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines.
abstract: Iodonium compounds play a pivotal role in (18) F-fluorination of radiopharmaceuticals containing non-activated arenes. However, preparation of these species is limited to oxidation conditions or exchange with organometallics that are prepared from aryl halides. Herein we describe a novel "one-pot" process to assemble aryl(isoquinoline)iodonium salts in 40-94 % yields from mesoionic carbene silver complex and Aryl-I-Py2 (OTf)2 . The method is general, practical, and compatible with well-functionalized molecules as well as useful for the preparation of a wide range of (18) F-labeled isoquinolines resulting in up to 92 % radiochemical conversion. As proof of concept, a fluorinated isoquinoline alkaloid, (18) F-aspergillitine is prepared in 10 % isolated radiochemical yield from the corresponding phenyl(aspergillitine)iodonium salt.
authors.affiliation: State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Road, Shanghai, 200032 (China).
authors.forename: Zheliang
authors.initials: Z
authors.lastname: Yuan
authors.affiliation: School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, 300072, China.|Gordon Center for Medical Imaging & Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital and Harvard Medical School, 55 Fruit St., Boston, MA (USA).
authors.forename: Ran
authors.initials: R
authors.lastname: Cheng
authors.affiliation: State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Road, Shanghai, 200032 (China).
authors.forename: Pinhong
authors.initials: P
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Road, Shanghai, 200032 (China).
authors.forename: Guosheng
authors.initials: G
authors.lastname: Liu
authors.affiliation: Gordon Center for Medical Imaging & Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital and Harvard Medical School, 55 Fruit St., Boston, MA (USA).
authors.forename: Steven H
authors.initials: SH
authors.lastname: Liang
mesh_terms: D000586:Amination; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods; D002867:Chromones / Q000138:chemical synthesis / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry; D054879:Halogenation; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009861:Onium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D049268:Positron-Emission Tomography; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000737:chemistry; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry; D012834:Silver / Q000737:chemistry
chemical_list: D002867:Chromones; D005462:Fluorine Radioisotopes; D006575:Heterocyclic Compounds, 3-Ring; D007546:Isoquinolines; D009861:Onium Compounds; D019275:Radiopharmaceuticals; D012492:Salts; C474263:aspergillitine; D012834:Silver
keywords: [18F]isoquinolines; carbene silver complexes; diaryliodonium salts; fluorine-18; positron emission tomography