Literature DB >> 30605563

Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C-H Bonds with K18 F.

So Jeong Lee1, Katarina J Makaravage2, Allen F Brooks1, Peter J H Scott1, Melanie S Sanford2.   

Abstract

A Cu-mediated ortho-C-H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18 F and is compatible with a wide range of functional groups. The reaction is showcased in the high specific activity automated synthesis of the RARβ2 agonist [18 F]AC261066.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H fluorination; C−H functionalization; PET radiochemistry; fluorine-18; late-stage fluorination

Year:  2019        PMID： 30605563      PMCID： PMC6476334          DOI： 10.1002/anie.201812701

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


  32 in total

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Review 2.  Molecular imaging with PET.

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4.  A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging.

Authors:  Eunsung Lee; Adam S Kamlet; David C Powers; Constanze N Neumann; Gregory B Boursalian; Takeru Furuya; Daniel C Choi; Jacob M Hooker; Tobias Ritter
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5.  Nickel-mediated oxidative fluorination for PET with aqueous [18F] fluoride.

Authors:  Eunsung Lee; Jacob M Hooker; Tobias Ritter
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Review 6.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

7.  A general copper-mediated nucleophilic 18F fluorination of arenes.

Authors:  Matthew Tredwell; Sean M Preshlock; Nicholas J Taylor; Stefan Gruber; Mickael Huiban; Jan Passchier; Joël Mercier; Christophe Génicot; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

8.  Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors:  Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

9.  Positron emission tomography (PET) imaging with (18)F-based radiotracers.

Authors:  Mian M Alauddin
Journal:  Am J Nucl Med Mol Imaging       Date:  2011-12-15

10.  Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts.

Authors:  Naoko Ichiishi; Allen F Brooks; Joseph J Topczewski; Melissa E Rodnick; Melanie S Sanford; Peter J H Scott
Journal:  Org Lett       Date:  2014-06-03       Impact factor: 6.005
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  7 in total

1.  NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides.

Authors:  Liam S Sharninghausen; Allen F Brooks; Wade P Winton; Katarina J Makaravage; Peter J H Scott; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2020-04-10       Impact factor: 15.419

2.  Synthesis of [18F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous 18F-fluorination of α-diazoacetates with [18F]AgF.

Authors:  Stephen Thompson; So Jeong Lee; Isaac M Jackson; Naoko Ichiishi; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  Synthesis (Stuttg)       Date:  2019-12       Impact factor: 3.157

Review 3.  Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Authors:  Yunze Wang; Qingyu Lin; Hongcheng Shi; Dengfeng Cheng
Journal:  Front Chem       Date:  2022-06-29       Impact factor: 5.545

4.  Synthesis of high-molar-activity [18F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

Authors:  Andrew V Mossine; Sean S Tanzey; Allen F Brooks; Katarina J Makaravage; Naoko Ichiishi; Jason M Miller; Bradford D Henderson; Thomas Erhard; Christian Bruetting; Marc B Skaddan; Melanie S Sanford; Peter J H Scott
Journal:  Nat Protoc       Date:  2020-04-08       Impact factor: 13.491

5.  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

6.  Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes.

Authors:  Jay S Wright; Liam S Sharninghausen; Sean Preshlock; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  J Am Chem Soc       Date:  2021-04-29       Impact factor: 15.419

7.  Alcohol-Supported Cu-Mediated 18F-Fluorination of Iodonium Salts under "Minimalist" Conditions.

Authors:  Victoriya V Orlovskaya; Daniel J Modemann; Olga F Kuznetsova; Olga S Fedorova; Elizaveta A Urusova; Niklas Kolks; Bernd Neumaier; Raisa N Krasikova; Boris D Zlatopolskiy
Journal:  Molecules       Date:  2019-09-03       Impact factor: 4.411
  7 in total

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