Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

doi:10.1021/acs.orglett.5b02875

. 2015 Dec 4;17(23):5780-3.

doi: 10.1021/acs.orglett.5b02875. Epub 2015 Nov 14.

Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

Andrew V Mossine¹, Allen F Brooks¹, Katarina J Makaravage², Jason M Miller³, Naoko Ichiishi², Melanie S Sanford², Peter J H Scott^{1

3}

Affiliations

¹ Department of Radiology, University of Michigan Medical School , 1301 Catherine Street, Ann Arbor, Michigan 48109, United States.
² Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
³ Department of Medicinal Chemistry, University of Michigan , 428 Church Street, Ann Arbor, Michigan 48109, United States.

PMID: 26568457
PMCID: PMC4672358
DOI: 10.1021/acs.orglett.5b02875

Free PMC article

Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

Andrew V Mossine et al. Org Lett. 2015.

Free PMC article

. 2015 Dec 4;17(23):5780-3.

doi: 10.1021/acs.orglett.5b02875. Epub 2015 Nov 14.

Authors

Andrew V Mossine¹, Allen F Brooks¹, Katarina J Makaravage², Jason M Miller³, Naoko Ichiishi², Melanie S Sanford², Peter J H Scott^{1

3}

Affiliations

¹ Department of Radiology, University of Michigan Medical School , 1301 Catherine Street, Ann Arbor, Michigan 48109, United States.
² Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
³ Department of Medicinal Chemistry, University of Michigan , 428 Church Street, Ann Arbor, Michigan 48109, United States.

PMID: 26568457
PMCID: PMC4672358
DOI: 10.1021/acs.orglett.5b02875

Abstract

A copper-mediated radiofluorination of aryl- and vinylboronic acids with K(18)F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [(18)F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.

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Figures

**Scheme 1. Nucleophilic Fluorination of Aryl Boron Reagents**

**Scheme 2. Radiofluorination of 1-BPin To Form [¹⁸F]-4-Fluoroacetophenone 2**

**Figure 1**
Substrate scope. Conditions: 1:5:125 boronic acid:CuOTf₂:pyridine at 4 mM concentration of the boronic acid precursor in DMF, K¹⁸F, 110 °C, 20 min.

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References

1. For a review of PET, see:Ametamey S. M.; Honer M.; Schubiger P. A. Chem. Rev. 2008, 108, 1501.10.1021/cr0782426. - DOI - PubMed
1. Van der Veldt A. A. M.; Lubberink M.; Mathijssen R. H. J.; Loos W. J.; Herder G. J. M.; Greuter H. N.; Comans E. F. I.; Rutten H. B.; Eriksson J.; Windhorst A. D.; Hendrikse N. H.; Postmus P. E.; Smit E. F.; Lammertsma A. A. Clin. Cancer Res. 2013, 19, 4163.10.1158/1078-0432.CCR-12-3779. - DOI - PubMed
1. Van den Abbeele A. D. Oncologist 2008, 13Suppl 28.10.1634/theoncologist.13-S2-8. - DOI - PubMed
2. Prior J. O.; Montemurro M.; Orcurto M. V.; Michielin O.; Luthi F.; Benhattar J.; Guillou L.; Elsig V.; Stupp R.; Delaloye A. B.; Leyvraz S. J. Clin. Oncol. 2008, 27, 439.10.1200/JCO.2008.17.2742. - DOI - PubMed
1. Miller P. W.; Long N. J.; Vilar R.; Gee A. D. Angew. Chem., Int. Ed. 2008, 47, 8998.10.1002/anie.200800222. - DOI - PubMed
2. Cai L.; Lu S.; Pike V. W. Eur. J. Org. Chem. 2008, 2008, 2853.10.1002/ejoc.200800114. - DOI
3. Littich R.; Scott P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.10.1002/anie.201106785. - DOI - PubMed
4. Brooks A. F.; Topczewski J. J.; Ichiishi N.; Sanford M. S.; Scott P. J. H. Chem. Sci. 2014, 5, 4545.10.1039/C4SC02099E. - DOI - PMC - PubMed
5. Cole E. L.; Stewart M. N.; Littich R.; Hoareau R.; Scott P. J. H. Curr. Top. Med. Chem. 2014, 14, 875.10.2174/1568026614666140202205035. - DOI - PMC - PubMed
6. Liang S. H.; Vasdev N. Angew. Chem., Int. Ed. 2014, 53, 11416.10.1002/anie.201407065. - DOI - PMC - PubMed
1. Wang J.; Sánchez-Roselló M.; Aceña J. L.; del Pozo C.; Sorochinsky A. E.; Fustero S.; Soloshonok V. A.; Liu H. Chem. Rev. 2014, 114, 2432.10.1021/cr4002879. - DOI - PubMed
2. Gillis E. P.; Eastman K. J.; Donnelly D. J.; Meanwell N. A. J. Med. Chem. 2015, 10.1021/acs.jmedchem.5b00258. - DOI - PubMed

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[1] For a review of PET, see:Ametamey S. M.; Honer M.; Schubiger P. A. Chem. Rev. 2008, 108, 1501.10.1021/cr0782426. - DOI - PubMed

[2] For a review of PET, see:Ametamey S. M.; Honer M.; Schubiger P. A. Chem. Rev. 2008, 108, 1501.10.1021/cr0782426. - DOI - PubMed

[3] Van der Veldt A. A. M.; Lubberink M.; Mathijssen R. H. J.; Loos W. J.; Herder G. J. M.; Greuter H. N.; Comans E. F. I.; Rutten H. B.; Eriksson J.; Windhorst A. D.; Hendrikse N. H.; Postmus P. E.; Smit E. F.; Lammertsma A. A. Clin. Cancer Res. 2013, 19, 4163.10.1158/1078-0432.CCR-12-3779. - DOI - PubMed

[4] Van der Veldt A. A. M.; Lubberink M.; Mathijssen R. H. J.; Loos W. J.; Herder G. J. M.; Greuter H. N.; Comans E. F. I.; Rutten H. B.; Eriksson J.; Windhorst A. D.; Hendrikse N. H.; Postmus P. E.; Smit E. F.; Lammertsma A. A. Clin. Cancer Res. 2013, 19, 4163.10.1158/1078-0432.CCR-12-3779. - DOI - PubMed

[5] Van den Abbeele A. D. Oncologist 2008, 13Suppl 28.10.1634/theoncologist.13-S2-8. - DOI - PubMed

Prior J. O.; Montemurro M.; Orcurto M. V.; Michielin O.; Luthi F.; Benhattar J.; Guillou L.; Elsig V.; Stupp R.; Delaloye A. B.; Leyvraz S. J. Clin. Oncol. 2008, 27, 439.10.1200/JCO.2008.17.2742. - DOI - PubMed

[6] Van den Abbeele A. D. Oncologist 2008, 13Suppl 28.10.1634/theoncologist.13-S2-8. - DOI - PubMed

[7] Prior J. O.; Montemurro M.; Orcurto M. V.; Michielin O.; Luthi F.; Benhattar J.; Guillou L.; Elsig V.; Stupp R.; Delaloye A. B.; Leyvraz S. J. Clin. Oncol. 2008, 27, 439.10.1200/JCO.2008.17.2742. - DOI - PubMed

[8] Miller P. W.; Long N. J.; Vilar R.; Gee A. D. Angew. Chem., Int. Ed. 2008, 47, 8998.10.1002/anie.200800222. - DOI - PubMed

Cai L.; Lu S.; Pike V. W. Eur. J. Org. Chem. 2008, 2008, 2853.10.1002/ejoc.200800114. - DOI

Littich R.; Scott P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.10.1002/anie.201106785. - DOI - PubMed

Brooks A. F.; Topczewski J. J.; Ichiishi N.; Sanford M. S.; Scott P. J. H. Chem. Sci. 2014, 5, 4545.10.1039/C4SC02099E. - DOI - PMC - PubMed

Cole E. L.; Stewart M. N.; Littich R.; Hoareau R.; Scott P. J. H. Curr. Top. Med. Chem. 2014, 14, 875.10.2174/1568026614666140202205035. - DOI - PMC - PubMed

Liang S. H.; Vasdev N. Angew. Chem., Int. Ed. 2014, 53, 11416.10.1002/anie.201407065. - DOI - PMC - PubMed

[9] Miller P. W.; Long N. J.; Vilar R.; Gee A. D. Angew. Chem., Int. Ed. 2008, 47, 8998.10.1002/anie.200800222. - DOI - PubMed

[10] Cai L.; Lu S.; Pike V. W. Eur. J. Org. Chem. 2008, 2008, 2853.10.1002/ejoc.200800114. - DOI

[11] Littich R.; Scott P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.10.1002/anie.201106785. - DOI - PubMed

[12] Brooks A. F.; Topczewski J. J.; Ichiishi N.; Sanford M. S.; Scott P. J. H. Chem. Sci. 2014, 5, 4545.10.1039/C4SC02099E. - DOI - PMC - PubMed

[13] Cole E. L.; Stewart M. N.; Littich R.; Hoareau R.; Scott P. J. H. Curr. Top. Med. Chem. 2014, 14, 875.10.2174/1568026614666140202205035. - DOI - PMC - PubMed

[14] Liang S. H.; Vasdev N. Angew. Chem., Int. Ed. 2014, 53, 11416.10.1002/anie.201407065. - DOI - PMC - PubMed

[15] Wang J.; Sánchez-Roselló M.; Aceña J. L.; del Pozo C.; Sorochinsky A. E.; Fustero S.; Soloshonok V. A.; Liu H. Chem. Rev. 2014, 114, 2432.10.1021/cr4002879. - DOI - PubMed

Gillis E. P.; Eastman K. J.; Donnelly D. J.; Meanwell N. A. J. Med. Chem. 2015, 10.1021/acs.jmedchem.5b00258. - DOI - PubMed

[16] Wang J.; Sánchez-Roselló M.; Aceña J. L.; del Pozo C.; Sorochinsky A. E.; Fustero S.; Soloshonok V. A.; Liu H. Chem. Rev. 2014, 114, 2432.10.1021/cr4002879. - DOI - PubMed

[17] Gillis E. P.; Eastman K. J.; Donnelly D. J.; Meanwell N. A. J. Med. Chem. 2015, 10.1021/acs.jmedchem.5b00258. - DOI - PubMed

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Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

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Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

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