Publications

2017 to present

230 Fluorspar to fluorochemicals upon low-temperature activation in water

I. Klose, C. Patel, A. Mondal, A. Schwarz, G. Pupo, V. Gouverneur

Nature 2024, 635, 359–364, DOI: 10.1038/s41586-024-08125-1

229 ¹⁸F‑Difluoromethyl(ene) Motifs via Oxidative Fluorodecarboxylation with [¹⁸F]Fluoride

S. Ortalli, J. Ford, R. Szpera, B. Stoessel, A. A. Trabanco, M. Tredwell, V. Gouverneur

Org. Lett. 2024, 26, 9368–9372, DOI: 10.1021/acs.orglett.4c03611

228 Nucleophilic Fluoride Anion Delivery from Triazacyclononane-Supported Molecular Ca–F Complexes

O. Apolinar, J. J. C. Struijs, D. Sarkar, V. Gouverneur, S. Aldridge

Angew. Chem. Int. Ed. 2024, DOI: 10.1002/anie.202414790

227 Enabling nucleophilic reactivity in molecular calcium fluoride complexes

J. J. C. Struijs, M. A. Ellwanger, A. E. Crumpton, V. Gouverneur, S. Aldridge

Nat. Chem. 2024, 16, 1473–1480, DOI: 10.1038/s.41557-024-01524-x

226 Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines

S. Ortalli, J. Ford, A. A. Trabanco, M. Tredwell, V. Gouverneur

J. Am. Chem. Soc. 2024, 146, 11599–11604, DOI: 10.1021/jacs.4c02474

Highlighted in: Photocatalytic Radiolabeling with ¹⁸F in Flow! on HepatoChem.

225 The ¹⁸F-Difluoromethyl Group: Challenges, Impact and Outlook

J. Ford, S. Ortalli, V. Gouverneur

Angew. Chem. Int. Ed. 2024, e202404957, DOI: 10.1002/anie.202404957

224 Expedient access to ¹⁸F-Fluoroheteroarenes via Deaminative Radiofluorination of Aniline-Derived Pyridinium Salts

J. Ford, S. Ortalli, Z. Chen, J. B. I. Sap, M. Tredwell, V. Gouverneur

Angew. Chem. Int. Ed. 2024, e202404945, DOI: 10.1002/anie.202404945

223 Mechanochemical difluoromethylation of (thio)phenols and N-heterocycles

J. Ford, B. Hopkin, J. B. I. Sap, V. Gouverneur

Isr. J. Chem. 2023, e202300109, DOI: 10.1002/ijch.202300109

222 Fluorochemicals from fluorspar via a phosphate-enabled mechanochemical process that bypasses HF

C. Patel, E. André-Joyaux, J. A. Leitch, X. Martínez De Irujo-Labalde, F. Ibba, J. Struijs, M. A. EllWanger, R. Paton, D. L. Browne, G. Pupo, S. Aldridge, M. A. Hayward, V. Gouverneur

Science 2023, 381, 302–306, DOI: 10-1126/science.adi1557

Highlighted in: Oxford team leads biomimetic fluorocarbon breakthrough on The Engineer, Nature inspires breakthrough achievement: Hazard-free production of fluorochemicals on Phys.org, Widely-used chemicals can now be made without releasing toxic gas on New Scientist and Nature inspires breakthrough achievement: hazard-free production of fluorochemicals on EurekAlert.

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221 Regiodivergent Nucleophilic Fluorination under Hydrogen Bonding Catalysis: A Computational and Experimental Study

M. A. Horwitz, A. B. Dürr, K. Afratis, Z. Chen, J. Soika, K. E. Christensen, M. Fushimi, R. S. Paton, V. Gouverneur

J. Am. Chem. Soc. 2023, 145, 9708–9717, DOI: 10.1021/jacs.3c01303

220 Posttranslational, site-directed photochemical fluorine editing of protein sidechains to probe residue oxidation state via ¹⁹F-nuclear magnetic resonance

P. G. Isenegger, B. Josephson, B. Gaunt, M. J. Davy, V. Gouverneur, A. J. Baldwin, B. G. Davis

Nat. Protoc. 2023, 18, 1543–1562, DOI: 10.1038/s41596-022-00800-9

219 A radioiodinated rucaparib analogue as an Auger electron emitter for cancer therapy

G. Destro, Z. Chen, C. Y. Chan, C. Fraser, G. Dias, M. Mosley, F. Guibbal, V. Gouverneur, B. Cornelissen

Nucl. Med. Bio. 2023, 116–117, 108312, DOI: 10.1016/j.nucmedbio.2022.108312

218 Correlation between molar activity, injection mass and uptake of the PARP targeting radiotracer [¹⁸F]olaparib in mouse models of glioma

C. Y. Chan, S. L. Hopkins, F. Guibbal, A. Pacelli, J. Baguña Torres, M. Mosley, D. Lau, P. Isenegger, Z. Chen, T. C. Wilson, G. Dias, R. Hueting, V. Gouverneur, B. Cornelissen

EJNMMI Res 2022, 12, 67. DOI: 10.1186/s13550-022-00940-9

217 Imaging PARP with [¹⁸F]rucaparib in pancreatic cancer models

C. Y. Chan, Z. Chen, G. Destro, M. Veal, D. Lau, E. O'Neill, G. Dias, M. Mosley, V. Kersemans, F. Guibbal, V. Gouverneur, B. Cornelissen

Eur J Nucl Med Mol Imaging 2022, 49, 3668–3678. DOI: 10.1007/s00259-022-05835-4

216 [¹⁸F]Difluorocarbene for Positron Emission Tomography

J. B. I. Sap, C. F. Meyer, J. Ford, N. J. W. Straathof, A. B. Dürr, M. J. Lelos, S. J. Paisey, T. A. Mollner, S. M. Hell, A. A. Trabanco, C. Genicot, C. W. am Ende, R. S. Paton, M. Tredwell, V. Gouverneur

Nature 2022, 606, 102–108. DOI:10.1038/s41586-022-04669-2

215 Multi-patient dose synthesis of [¹⁸F]Flumazenil via a copper-mediated ¹⁸F-fluorination

T. Gendron, G. Destro, N. J. W. Straathof, J. B. I. Sap, F. Guibbal, C. Vriamont, C. Caygill, J. R. Atack, A. J. Watkins, C. Marshall, R. Hueting, C. Warnier, V. Gouverneur, M. Tredwell

EJNMMI radiopharm. chem. 2022, 7, 5. DOI:10.1186/s41181-022-00158-z

214 Hydrogen Bonding Phase-Transfer Catalysis with Alkali Metal Fluorides and Beyond

G. Pupo, V. Gouverneur

J. Am. Chem. Soc. 2022, 144, 5200–5213. DOI:10.1021/jacs.2c00190

213 Asymmetric Azidation under Hydrogen Bonding Phase-Transfer Catalysis: A Combined Experimental and Computational Study

J. Wang, M. A. Horwitz, A. B. Dürr, F. Ibba, G. Pupo, Y. Gao, P. Ricci, K. E. Christensen, T. P. Pathak, T. D. W. Claridge,G. C. Lloyd-Jones,R. S. Paton, V. Gouverneur

J. Am. Chem. Soc. 2022, 144, 4572–4584. DOI:10.1021/jacs.1c13434

212 Scalable Synthesis of (R,R)-N,N-Dibenzyl-2-fluorocyclohexan-1-amine with CsF under Hydrogen Bonding Phase-Transfer Catalysis

A. C. Vicini, D-M Alozie, P. Courtes, G. Roagna, C. Aubert, V. Certal, Y. El-Ahmad, S. Roy, V. Gouverneur

Org. Process Res. Dev. 2021, 25, 2730–2737. DOI:10.1021/acs.oprd.1c00312

211 Multigram synthesis of N-alkyl bis-ureas for asymmetric hydrogen bonding phase-transfer catalysis

A. C. Vicini, G. Pupo, F. Ibba, V. Gouverneur

Nat. Protoc. 2021, 16, 5559–5591. DOI:10.1038/s41596-021-00625-y

Highlighted in: Protocols & Methods Community

210 Post-translational insertion of boron in proteins to probe and modulate function

T. A. Mollner, P. G. Isenegger, B. Josephson, C. Buchanan, L. Lercher, D. Oehlrich, D. Flemming Hansen, S. Mohammed, A. J. Baldwin, V. Gouverneur, B. G. Davis

Nat. Chem. Biol. 2021, 17, 1245–1261. DOI:10.1038/s41589-021-00883-7

209 Closing the gap between ¹⁹F and ¹⁸F chemistry

J. Ajenjo, G. Destro, F. Guibbal, B. Cornelissen, V. Gouverneur

EJNMMI radiopharm. chem. 2021, 6, 33. DOI:10.1186/s41181-021-00143-y

208 Copper-Mediated Radiosynthesis of [¹⁸F]Rucaparib

Z. Chen, G. Destro, F. Guibbal, C. Y. Chan, B. Cornelissen, V. Gouverneur

Org. Lett. 2021, 23, 7290–7294. DOI:10.1021/acs.orglett.1c02770

207 Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond

S. M. Hell, C. F. Meyer, S. Ortalli, J. Sap, X. Chen, V. Gouverneur

Chem. Sci. 2021, 12, 12149–12155. DOI:10.1039/d1sc03421a

206 Contemporary synthetic strategies in organofluorine chemistry

R. Britton, V. Gouverneur, J.-H Lin, M. Meanwell, C. Ni, G. Pupo, J.-C. Xiao, J. Hu

Nat. Rev. Methods Primers. 2021, 1, 47. DOI:10.1038/s43586-021-00042-1

205 Late-stage difluoromethylation: concepts, developments and perspective

J. B. I. Sap, C. F. Meyer, N. J. W. Straathof, N. Iwumene, C. W. am Ende, A. A. Trabanco, V. Gouverneur

Chem. Soc. Rev. 2021, 50, 8214–8247. DOI:10.1039/D1CS00360G

204 Residue-Selective Protein C-Formylation via Sequential Difluoroalkylation-Hydrolysis

M. Imiołek, P. G. Isenegger, W. Ng, A. Khan, V. Gouverneur, B. G. Davis

ACS Cent. Sci. 2021, 7, 145–155. DOI:10.1021/acscentsci.0c01193

203 ¹⁸F-meta-fluorobenzylguanidine (¹⁸F-mFBG) to monitor changes in norepinephrine transporter expression in response to therapeutic intervention in neuroblastoma models

S. Turnock, D. R. Turton, C. D. Martins, L. Chesler, T. C. Wilson, V. Gouverneur, G. Smith, G. Kramer-Marek

Sci. Rep. 2020, 10, 1–12. DOI:10.1038/s41598-020-77788-3

202 Impact of Multiple Hydrogen Bonds with Fluoride on Catalysis: Insight from NMR Spectroscopy

F. Ibba, G. Pupo, A. L. Thompson, J. M. Brown, T. D. W. Claridge, V. Gouverneur

J. Am. Chem. Soc. 2020, 142, 19731–19744. DOI:10.1021/jacs.0c09832

201 Light-driven post-translational installation of reactive protein side chains

B. Josephson, C. Fehl, P. G. Isenegger, S. Nadal, T. H. Wright, A. W. J. Poh, B. J. Bower, A. M. Giltrap, L. Chen, C. Batchelor-McAuley, G. Roper, O. Arisa, J. B. I. Sap, A. Kawamura, A. J. Baldwin, S. Mohammed, R. G. Compton, V. Gouverneur, B. G. Davis

Nature 2020, 585, 530–537. DOI:10.1038/s41586-020-2733-7

Highlighted in: Radical post-translational modifications

Chemistry World 2021

200 Radiosynthesis of [¹⁸F]ArylSCF2H using aryl boronic acids, S-(chlorofluoromethyl)benzenesulfonothioate and [¹⁸F]fluoride

Q. Zhao, P. G. Isenegger, T. C. Wilson, J. B. I. Sap, F. Guibbal, L. Lu, V. Gouverneur, Q. Shen

Chinese Chem. Soc. Chem. 2020, 2, 1921–1928. DOI:10.31635/ccschem.020.202000399

199 Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling

R. Szpera, P. G. Isenegger, M. Ghosez, N. J. W. Straathof, R. Cookson, D. C. Blakemore, P. Richardson, V. Gouverneur

Org. Lett. 2020, 22, 6573–6577. DOI:10.1021/acs.orglett.0c02347

198 Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines

G. Roagna, D. Ascough, F. Ibba, A. C. Vicini, A. Fontana, K. Christensen, A. Peschiulli, D. Oehlrich, M. Misale, A. Trabanco, R. Paton, G. Pupo, V. Gouverneur

J. Am. Chem. Soc. 2020, 142, 14045–14051. DOI:10.1021/jacs.0c05131

This publication is also available as a Live Slide format

Highlighted in: Bisurea-Catalyzed Enantioselective Synthesis of γ-Fluoroamines

Synfacts 2020, 16, 1099–1100

197 Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery

J. B. I. Sap, N. J. W. Straathof, T. Knauber, C. F. Meyer, M. Médebielle, L. Buglioni, C. Genicot,A. A. Trabanco,T. Noël, C. W. am Ende, V. Gouverneur

J. Am. Chem. Soc. 2020, 142, 9181–9187. DOI:10.1021/jacs.0c03881

Highlighted in: Some Items of Interest to Process R&D Chemists and Engineers

W. Zhao, S. Guizzetti, J. A. Schwindeman, D. S. B. Daniels, J. J. Douglas, S. Petit, C. B. Kelly, A. Kosanovich, J. Knight

Org. Process Res. Dev. 2020, 24, 1351–1363

196 [¹⁸F]AZD2461, an Insight on Difference in PARP Binding Profiles for DNA Damage Response PET Imaging

F. Guibbal, S. L. Hopkins, A. Pacelli, P. G. Isenegger, M. Mosley, J. B. Torres, G. M. Dias, D. Mahaut, R. Hueting, V. Gouverneur, B. Cornelissen

Mol Imaging Biol. 2020, 22, 1226–1234. DOI:10.1007/s11307-020-01497-6

195 Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

S. M. Hell,C. F. Meyer, A. Misale, J. B. Sap, K. E. Christensen, M. C. Willis, A. A. Trabanco, V. Gouverneur

Angew. Chem. Int. Ed. 2020, 59, 11620–11626. DOI:10.1002/anie.202004070

194 Manual and automated Cu-mediated radiosynthesis of the PARP inhibitor [¹⁸F]olaparib

F. Guibbal, P. G. Isenegger, T. C. Wilson, A. Pacelli, D. Mahaut, J. B. I. Sap, N. J. Taylor, S. Verhoog, S. Preshlock, R. Hueting, B. Cornelissen, V. Gouverneur

Nat Protoc. 2020, 15, 1525–1541. DOI:10.1038/s41596-020-0295-7

193 ¹⁸F-Trifluoromethanesulfinate enables Direct C–H ¹⁸F-Trifluoromethylation of Native Aromatic Residues in Peptides

C. W. Kee, O. Tack, F. Guibbal, T. C. Wilson, P. G. Isenegger, M. Imiołek, S Verhoog, M. Tilby, G. Boscutti, S. Ashworth, J Chupin, R. Kashani, A. W. J. Poh, J. K. Sosabowski, S. Macholl, C. Plisson, B. Cornelissen, M. C. Willis, J. Passchier, B. G. Davis, V. Gouverneur

J. Am. Chem. Soc. 2020, 142, 1180–1185. DOI:10.1021/jacs.9b11709

192 Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkene

S. M. Hell, C. F. Meyer, G. Laudadio, A. Misale, M. C. Willis, T. Noel, A. A. Trabanco, V. Gouverneur

J. Am. Chem. Soc. 2020, 142, 720–725. DOI:10.1021/jacs.9b13071

Highlighted in: Easy Access to Aliphatic Sulfonamides using Sulfamoyl Chlorides Under Visible Light Activation

S. M. Hell, C. F. Meyer, A. A. Trabanco, V. Gouverneur

J. Vis. Exp. 2020, e6138

Highlighted on the Organic Chemistry Portal

191 Hydrochlorofluoromethylation of Unactivated Alkenes with Chlorofluoroacetic Acid

C. F. Meyer, S. M. Hell, J. B. I. Sap, A. Misale, A. Peschiulli, D. Oehlrich, A. A. Trabanco, V. Gouverneur

Invited contribution to the special issue in honour of Professor Steve Davies.

Tetrahedron 2019, 75, 130679–130680. DOI:10.1016/j.tet.2019.130679

190 Imaging of translocator protein upregulation is selective for pro-inflammatory polarised astrocytes and microglia

M. Pannell, V. Economopoulos, T. C. Wilson, V. Kersemans, P. G. Isenegger, J. R. Larkin, S. Smart, S. Gilchrist, V. Gouverneur, N. R. Sibson

GLIA 2019, 68, 280–297. DOI:10.1002/glia.23716

189 In My Element: Fluorine

V. Gouverneur

In My Element series celebrates the personal accounts from Chemistry - A European Journal Editorial Board members for the 2019 International Year
of the Periodic Table.

Chem. Eur. J. 2019, 25, 7958–7959. DOI:10.1002/chem.201902265

188 Hydrodifluoromethylation of Alkenes with Difluoroacetic Acid

C. F. Meyer, S. M. Hell, A. Misale, A. A. Trabanco, V. Gouverneur

Angew. Chem. Int. Ed. 2019, 58, 8828–8833. DOI:10.1002/anie.201903801

187 The fluorination of C–H bonds: developments and perspectives

R. Szpera, D. F. J. Moseley, L. B. Smith, A. J. Sterling, V. Gouverneur

Angew. Chem. Int. Ed. 2019, 58, 14824–14848. DOI:10.1002/anie.201814457

186 Synthesis of ¹⁸F-Difluoromethylarenes Using Aryl Boronic Acids, Ethyl bromofluoroacetate and [¹⁸F]Fluoride

J. B. I. Sap, T. C. Wilson, C. W. Kee, N. J. W. Straathof, C. W. Amende, P. Mukherjee, L. Zhang, C. Genicot, V. Gouverneur

Chem. Sci. 2019, 10, 3237–3241. DOI: 10.1039/C8SC05096A

185 Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines

G. Pupo, A. C. Vicini, D. M. H. Ascough, F. Ibba, K. E. Christensen, A. L. Thompson, J. M. Brown, R. S. Paton, V. Gouverneur

J. Am. Chem. Soc. 2019, 141, 2878–2883. DOI: 10.1021/jacs.8b12568

184 Synthesis and Reactivity of a-Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [¹⁸F]ArylSCF₃

J. Wu, Q. Zhao, T. C. Wilson, S. Verhoog, L. Lu, V. Gouverneur and Q. Shen

Angew. Chem. Int. Ed. 2019, 58, 1–6. DOI: 10.1002/anie.20181370

183 Data-mining the diaryl(thio)urea conformational landscape: Understanding the contrasting behavior of ureas and thioureas with quantum chemistry

G. Luchini, D. M. H. Ascough, J. V. Alegre-Requena, V. Gouverneur, R. S. Paton

Special Issue Paper: Computational Chemistry in Organic Synthesis. Guest Editors: Dean Tantillo and John Wood

Tetrahedron 2019, 75, 69–-702. DOI: 10.1016/j.tet.2018.12.033

182 Enantioselective rhodium-catalysed insertion of trifluorodiazoethanes into tin hydrides

S. Hyde, J. Veliks, D. M. H. Ascough, R. Szpera, R. S. Paton, V. Gouverneur

Special Issue in honour of Prof Leon Ghosez

Tetrahedron 2019, 75, 17–25. DOI: 10.1016/j.tet.2018.11.022

181 PET Imaging of PARP Expression Using ¹⁸F-Olaparib

T. C. Wilson, M. A. Xavier, J. Knight, S. Verhoog, J. B. Torres, M. Mosley, S. L. Hopkins, S. Wallington, P. D. Allen, V. Kersemans, R. Hueting, S. Smart, V. Gouverneur, B. Cornelissen

J. Nucl. Med. 2018, 60, 504–510. DOI: 10.2967/jnumed.118.213223