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Title: Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K 18 F

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]
  1. Department of Radiology, University of Michigan, 1301 Catherine St Ann Arbor MI 48109 USA
  2. Department of Chemistry, The University of Michigan, 930 North University Ave Ann Arbor MI 48109 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1491271
Grant/Contract Number:  
SC0012484
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition) Journal Volume: 58 Journal Issue: 10; Journal ID: ISSN 1433-7851
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Lee, So Jeong, Makaravage, Katarina J., Brooks, Allen F., Scott, Peter J. H., and Sanford, Melanie S. Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K 18 F. Germany: N. p., 2019. Web. doi:10.1002/anie.201812701.
Lee, So Jeong, Makaravage, Katarina J., Brooks, Allen F., Scott, Peter J. H., & Sanford, Melanie S. Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K 18 F. Germany. doi:10.1002/anie.201812701.
Lee, So Jeong, Makaravage, Katarina J., Brooks, Allen F., Scott, Peter J. H., and Sanford, Melanie S. Fri . "Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K 18 F". Germany. doi:10.1002/anie.201812701.
@article{osti_1491271,
title = {Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C−H Bonds with K 18 F},
author = {Lee, So Jeong and Makaravage, Katarina J. and Brooks, Allen F. and Scott, Peter J. H. and Sanford, Melanie S.},
abstractNote = {},
doi = {10.1002/anie.201812701},
journal = {Angewandte Chemie (International Edition)},
number = 10,
volume = 58,
place = {Germany},
year = {2019},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/anie.201812701

Citation Metrics:
Cited by: 4 works
Citation information provided by
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Works referenced in this record:

Copper-Mediated Aromatic Radiofluorination Revisited: Efficient Production of PET Tracers on a Preparative Scale
journal, February 2015

  • Zlatopolskiy, Boris D.; Zischler, Johannes; Krapf, Philipp
  • Chemistry - A European Journal, Vol. 21, Issue 15
  • DOI: 10.1002/chem.201405586

Copper-Catalyzed [ 18 F]Fluorination of (Mesityl)(aryl)iodonium Salts
journal, June 2014

  • Ichiishi, Naoko; Brooks, Allen F.; Topczewski, Joseph J.
  • Organic Letters, Vol. 16, Issue 12
  • DOI: 10.1021/ol501243g

Molecular Imaging with PET
journal, May 2008

  • Ametamey, Simon M.; Honer, Michael; Schubiger, Pius August
  • Chemical Reviews, Vol. 108, Issue 5
  • DOI: 10.1021/cr0782426

A General Copper-Mediated Nucleophilic 18 F Fluorination of Arenes
journal, June 2014

  • Tredwell, Matthew; Preshlock, Sean M.; Taylor, Nicholas J.
  • Angewandte Chemie, Vol. 126, Issue 30
  • DOI: 10.1002/ange.201404436

Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes
journal, December 2014

  • Jacobson, Orit; Kiesewetter, Dale O.; Chen, Xiaoyuan
  • Bioconjugate Chemistry, Vol. 26, Issue 1
  • DOI: 10.1021/bc500475e

A General Copper-Mediated Nucleophilic 18 F Fluorination of Arenes
journal, June 2014

  • Tredwell, Matthew; Preshlock, Sean M.; Taylor, Nicholas J.
  • Angewandte Chemie International Edition, Vol. 53, Issue 30
  • DOI: 10.1002/anie.201404436

A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging
journal, November 2011


Concerted nucleophilic aromatic substitution with 19F− and 18F−
journal, May 2016

  • Neumann, Constanze N.; Hooker, Jacob M.; Ritter, Tobias
  • Nature, Vol. 534, Issue 7607
  • DOI: 10.1038/nature17667

Late-stage [ 18 F]fluorination: new solutions to old problems
journal, January 2014

  • Brooks, Allen F.; Topczewski, Joseph J.; Ichiishi, Naoko
  • Chem. Sci., Vol. 5, Issue 12
  • DOI: 10.1039/C4SC02099E

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design
journal, February 2018


Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)
journal, December 2013

  • Wang, Jiang; Sánchez-Roselló, María; Aceña, José Luis
  • Chemical Reviews, Vol. 114, Issue 4
  • DOI: 10.1021/cr4002879

Copper-Mediated Radiofluorination of Arylstannanes with [ 18 F]KF
journal, October 2016


Nickel-catalyzed selective C-5 fluorination of 8-aminoquinolines with NFSI
journal, January 2017

  • Ding, Junshuai; Zhang, Yingchao; Li, Jizhen
  • Organic Chemistry Frontiers, Vol. 4, Issue 8
  • DOI: 10.1039/C7QO00211D

Site-Selective, Late-Stage C−H 18 F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging
journal, September 2018

  • Yuan, Zheliang; Nodwell, Matthew B.; Yang, Hua
  • Angewandte Chemie International Edition, Vol. 57, Issue 39
  • DOI: 10.1002/anie.201806966

Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation
journal, March 2015

  • Huang, Xiongyi; Liu, Wei; Hooker, Jacob M.
  • Angewandte Chemie, Vol. 127, Issue 17
  • DOI: 10.1002/ange.201500399

Applications of Fluorine in Medicinal Chemistry
journal, July 2015


18 F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography
journal, January 2016


A cinchonidine derivative for photoaffinity labelling of proteins
journal, January 2000


Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds
journal, June 2013

  • Truong, Thanh; Klimovica, Kristine; Daugulis, Olafs
  • Journal of the American Chemical Society, Vol. 135, Issue 25
  • DOI: 10.1021/ja4047125

Automated synthesis of PET radiotracers by copper-mediated 18 F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation
journal, February 2018

  • Mossine, Andrew V.; Brooks, Allen F.; Bernard-Gauthier, Vadim
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 61, Issue 3
  • DOI: 10.1002/jlcr.3583

Development of 18F-labeled radiotracers for neuroreceptor imaging with positron emission tomography
journal, August 2014


Synthesis of [ 18 F]Arenes via the Copper-Mediated [ 18 F]Fluorination of Boronic Acids
journal, November 2015


Nickel-Mediated Oxidative Fluorination for PET with Aqueous [ 18 F] Fluoride
journal, October 2012

  • Lee, Eunsung; Hooker, Jacob M.; Ritter, Tobias
  • Journal of the American Chemical Society, Vol. 134, Issue 42
  • DOI: 10.1021/ja3084797

Discovery of a Potent, Orally Available, and Isoform-Selective Retinoic Acid β2 Receptor Agonist
journal, December 2005

  • Lund, Birgitte W.; Piu, Fabrice; Gauthier, Natalie K.
  • Journal of Medicinal Chemistry, Vol. 48, Issue 24
  • DOI: 10.1021/jm050891r

Modern Carbon–Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis
journal, August 2014

  • Campbell, Michael G.; Ritter, Tobias
  • Chemical Reviews, Vol. 115, Issue 2
  • DOI: 10.1021/cr500366b

Site-selective 18 F fluorination of unactivated C–H bonds mediated by a manganese porphyrin
journal, January 2018

  • Liu, Wei; Huang, Xiongyi; Placzek, Michael S.
  • Chemical Science, Vol. 9, Issue 5
  • DOI: 10.1039/C7SC04545J

Cu-Mediated C–H 18 F-Fluorination of Electron-Rich (Hetero)arenes
journal, June 2017


18 F-Deoxyfluorination of Phenols via Ru π-Complexes
journal, August 2017


Moving Metal-Mediated 18 F-Fluorination from Concept to Clinic
journal, March 2016


Fluorine-18-labeled fluorine gas for synthesis of tracer molecules
journal, October 1997


Derisking the Cu-Mediated 18 F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands
journal, June 2017

  • Taylor, Nicholas J.; Emer, Enrico; Preshlock, Sean
  • Journal of the American Chemical Society, Vol. 139, Issue 24
  • DOI: 10.1021/jacs.7b03131

Bridging the gaps in 18F PET tracer development
journal, December 2016

  • Campbell, Michael G.; Mercier, Joel; Genicot, Christophe
  • Nature Chemistry, Vol. 9, Issue 1
  • DOI: 10.1038/nchem.2693

18 F-Fluorination of Unactivated C–H Bonds in Branched Aliphatic Amino Acids: Direct Synthesis of Oncological Positron Emission Tomography Imaging Agents
journal, March 2017

  • Nodwell, Matthew B.; Yang, Hua; Čolović, Milena
  • Journal of the American Chemical Society, Vol. 139, Issue 10
  • DOI: 10.1021/jacs.6b11533

Late Stage Benzylic C–H Fluorination with [ 18 F]Fluoride for PET Imaging
journal, May 2014

  • Huang, Xiongyi; Liu, Wei; Ren, Hong
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja5039819

Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation
journal, March 2015

  • Huang, Xiongyi; Liu, Wei; Hooker, Jacob M.
  • Angewandte Chemie International Edition, Vol. 54, Issue 17
  • DOI: 10.1002/anie.201500399

Site-Selective, Late-Stage C−H 18 F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging
journal, September 2018

  • Yuan, Zheliang; Nodwell, Matthew B.; Yang, Hua
  • Angewandte Chemie, Vol. 130, Issue 39
  • DOI: 10.1002/ange.201806966