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
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 18 F-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 on: 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
X. Jiang
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
B. List, Y.Li
Synfacts 2020, 16, 1099–1100. DOI:10.1055/s-0040-1706771
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. DOI:10.1021/acs.oprd.0c00344
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 Alkenes
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. DOI:10.3791/61384
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, 697-702. 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
180 Boron reagents for divergent radiochemistry
T. C. Wilson, T. Cailly, V. Gouverneur
Chem Soc Rev. 2018, 47, 6990-7005. DOI: 10.1039/c8cs00499d
179 Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis
G. Pupo, F. Ibba, D. M. H. Ascough, A. C. Vicini, P. Ricci, K. E. Christensen, L. Pfeifer, J. R. Morphy, J. M. Brown, R. S. Paton, V. Gouverneur
Science 2018, 360, 638-642. DOI: 10.1126/science.aar7941
178 Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis
N. Punna, P. Das, V. Gouverneur, N. Shibata
Org. Lett. 2018, 20, 1526-1529. DOI: 10.1021/acs.orglett.8b00237
177 Controlled Single and Double Iodofluorination of Alkynes with DIH- and HF-Based Reagents
L. Pfeifer, V. Gouverneur
Org. Lett. 2018, 20, 1576-1579. DOI: 10.1021/acs.orglett.8b00321
176 Selective Radical Trifluoromethylation of Native Residues in Proteins
M. Imiołek, G. Karunanithy, W-L. Ng, A. J. Baldwin, V. Gouverneur, B. G. Davis
J. Am. Chem. Soc. 2018, 7, 1568-1571. DOI: 10.1021/jacs.7b10230
175 18F-Trifluoromethylation of Unmodified Peptides with 5-18F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate
S. Verhoog, C. W. Kee, Y. Wang, T. Khotavivattana, T. C. Wilson, V. Kersemans, S. Smart, M. Tredwell, B. G. Davis, V. Gouverneur
J. Am. Chem. Soc. 2018, 7, 1572-1575. DOI: 10.1021/jacs.7b10227
174 Synthesis, characterization, thermal and surface properties of co- and terpolymers based on fluorinated a-methylstyrenes and styrene
J. Walkowiak-Kulikowska, A. Szwajca, V. Gouverneur, B. Ameduri
Polym. Chem-Uk 2017, 8, 6558-6569. DOI: 10.1039/C7PY01529A
173 De-Risking the Cu-Mediated 18F-Fluorination of Heterocyclic PET Radioligands
N. J. Taylor, E. Emer, S. Preshlock, M. Schedler, M. Tredwell, S. Verhoog, J. Mercier, C. Genicot, V. Gouverneur
J. Am. Chem. Soc. 2017, 139, 8267-8276. DOI: 10.1021/jacs.7b03131
172 Synthesis and Reactivity of 18F-Labeled α,α-Difluoro-α-Aryloxyacetic Acids
T. Khotavivattana, S. Calderwood, S. Verhoog, L. Pfeifer, S. Preshlock, N. Vasdev, T. L. Collier, V. Gouverneur
Org. Lett. 2017, 19, 568-571. DOI: 10.1021/acs.orglett.6b03730
171 The Dual Role of Thiourea in the Thiotrifluoromethylation of Alkenes
P. Ricci, T. Khotavivattana, L. Pfeifer, M. Médebielle, J. R. Morphy, V. Gouverneur
Chem. Sci. 2017, 8, 1195-1199. DOI: 10.1039/C6SC02790C
170 Bridging the gaps in 18F PET tracer development
M. G. Campbell, J. Mercier, C. Genicot, V. Gouverneur, J. M. Hooker, T. Ritter
Nat. Chem. 2017, 9, 1-3. DOI: 10.1038/nchem.2693
169 Twisting the Ethano-Tröger’s Base: The Bisamide
R. Pereira, L. Pfeifer, J. Fournier, V. Gouverneur V, J. Cvengroš
Org. Biomol. Chem. 2017, 15, 628-633. DOI: 10.1039/C6OB02359B