Literature DB >> 25155042

A universal procedure for the [¹⁸F]trifluoromethylation of aryl iodides and aryl boronic acids with highly improved specific activity.

Dion van der Born1, Claudia Sewing, J Koos D M Herscheid, Albert D Windhorst, Romano V A Orru, Danielle J Vugts.   

Abstract

Herein, we describe a valuable method for the introduction of the [(18)F]CF3 group into arenes with highly improved specific activity by the reaction of [(18)F]trifluoromethane with aryl iodides or aryl boronic acids. This [(18)F]trifluoromethylation reaction is the first to be described in which the [(18)F]CF3 products are generated in actual trace amounts and can therefore effectively be used as PET tracers. The method shows broad scope with respect to possible aryl iodide and aryl boronic acid substrates, as well as good to excellent conversion. In particular, the [(18)F]trifluoromethylation of boronic acids was found to outperform [(18)F]trifluoromethylation reactions of halogenated aryl precursors with regard to conversion, reaction conditions, and kinetics.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  fluorine-18; isotopic labeling; radiochemistry; specific activity; trifluoromethylation

Mesh：

Substances：

Year:  2014        PMID： 25155042     DOI： 10.1002/anie.201406221

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  19 in total

1.  Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

Authors:  Hang Shi; Augustin Braun; Lu Wang; Steven H Liang; Neil Vasdev; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-05       Impact factor: 15.336

Review 2.  Fluorine-18 patents (2009-2015). Part 2: new radiochemistry.

Authors:  Andrew V Mossine; Stephen Thompson; Allen F Brooks; Alexandra R Sowa; Jason M Miller; Peter Jh Scott
Journal:  Pharm Pat Anal       Date:  2016-09

Review 3.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

4.  Syntheses of [11C]2- and [11C]3-trifluoromethyl-4-aminopyridine: potential PET radioligands for demyelinating diseases.

Authors:  Karla M Ramos-Torres; Yu-Peng Zhou; Bo Yeun Yang; Nicolas J Guehl; Moon Sung-Hyun; Sanjay Telu; Marc D Normandin; Victor W Pike; Pedro Brugarolas
Journal:  RSC Med Chem       Date:  2020-07-24

5.  A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation.

Authors:  Mark D Levin; Tiffany Q Chen; Megan E Neubig; Cynthia M Hong; Cyril A Theulier; Ilia J Kobylianskii; Mustafa Janabi; James P O'Neil; F Dean Toste
Journal:  Science       Date:  2017-06-23       Impact factor: 47.728

6.  Synthesis and Screening in Mice of Fluorine-Containing PET Radioligands for TSPO: Discovery of a Promising 18F-Labeled Ligand.

Authors:  Fabrice G Siméon; Jae-Hoon Lee; Cheryl L Morse; Ian Stukes; Sami S Zoghbi; Lester S Manly; Jeih-San Liow; Robert L Gladding; Rachel M Dick; Xuefeng Yan; Sabrina Taliani; Barbara Costa; Claudia Martini; Federico Da Settimo; Sabrina Castellano; Robert B Innis; Victor W Pike
Journal:  J Med Chem       Date:  2021-11-10       Impact factor: 7.446

7.  [11 C]Fluoroform, a Breakthrough for Versatile Labeling of PET Radiotracer Trifluoromethyl Groups in High Molar Activity.

Authors:  Mohammad B Haskali; Victor W Pike
Journal:  Chemistry       Date:  2017-05-17       Impact factor: 5.236

8.  Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors:  Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-21       Impact factor: 15.336

9.  N'-3-(Trifluoromethyl)phenyl Derivatives of N-Aryl-N'-methylguanidines as Prospective PET Radioligands for the Open Channel of the N-Methyl-d-aspartate (NMDA) Receptor: Synthesis and Structure-Affinity Relationships.

Authors:  Gregory R Naumiec; Kimberley J Jenko; Sami S Zoghbi; Robert B Innis; Lisheng Cai; Victor W Pike
Journal:  J Med Chem       Date:  2015-12-04       Impact factor: 7.446

10.  Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Authors:  Jay S Wright; Tanpreet Kaur; Sean Preshlock; Sean S Tanzey; Wade P Winton; Liam S Sharninghausen; Nicholas Wiesner; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  Clin Transl Imaging       Date:  2020-05-26
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