Copper‐Mediated Aminoquinoline‐Directed Radiofluorination of Aromatic C−H Bonds with K 18 F

Lee, So Jeong; Makaravage, Katarina J.; Brooks, Allen F.; Scott, Peter J. H.; Sanford, Melanie S.

doi:10.1002/ange.201812701

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

Authors:

^[1];

^[2];

^[1];

^[2]

Department of Radiology University of Michigan 1301 Catherine St Ann Arbor MI 48109 USA
Department of Chemistry The University of Michigan 930 North University Ave Ann Arbor MI 48109 USA

Publication Date:: 2019-01-18

Sponsoring Org.:: USDOE

OSTI Identifier:: 1493376

Grant/Contract Number:: SC0012484

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie

Additional Journal Information:: Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 10; Journal ID: ISSN 0044-8249

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/ange.201812701.

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                    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.  https://doi.org/10.1002/ange.201812701

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                    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.  https://doi.org/10.1002/ange.201812701.

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@article{osti_1493376,

  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/ange.201812701},

  journal      = {Angewandte Chemie},

  number       = 10,

  volume       = 131,

  place        = {Germany},

  year         = {2019},

  month        = {1}

}

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

Citation Formats

Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor: Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor journal, May 2018

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

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

Molecular Imaging with PET journal, May 2008

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor: Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor
journal, May 2018

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

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

Molecular Imaging with PET
journal, May 2008

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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