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Published on 9 May 2023
2023



Modern Strategies for Carbon Isotope Exchange

A. Labiche, A. Malandain, M. Molins, F. Taran, D. Audisio* 
Angew. Chem. Int. Ed. 2023, e202303535
Artwork : Clara Zavarise

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- Fast and Bioorthogonal Release of Isocyanates in Living Cells from IminoSydnones and Cycloalkynes

M. Ribéraud, K. Porte, A. Chevalier, L. Madegard, A. Rachet, A. Delaunay-Moisan, F. Vinchon, P. Thuéry, D. Audisio, F. Taran*
J. Am. Chem. Soc. 2023, 145, 2219-2229

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Correlative radioimaging and mass spectrometry imaging: a powerful combination to study 14C-graphene oxide in vivo biodistribution

H. Cazier, C. Malgorn, D. Georgin, N. Fresneau, F. Beau, K. Kostarelos, C. Bussy, S. Campidelli, M. Pinault, M. Mayne-L'Hermite, F. Taran, C. Junot, F. Fenaille, A. Sallustrau,* B. Colsch*
Nanoscale, 2023, 15, 5510–5518

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- Sydnone-Cyanines as clickable Probes for Fluorescent Labelling

K. A. Nguyen, E. Lesur, M. Ribéraud, A. Sallustrau, D. Audisio, F. Taran*
Helv. Chim. Acta 2023, 106, e202200187

- Continuous Flow Synthesis of Non-Symmetrical Ureas from CO2

A. Labiche, M. Norlöff, S. Feuillastre, F. Taran, D. Audisio*
Asian J. Org. Chem. 2023, 12, e202200640

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2022



Catalytic Methoxylation of Aryl Halides Using 13C- and 14C-Labeled CO2

A. Ohleier, A. Sallustrau, F. Caillé,* D. Audisio,* T. Cantat* 
Chem. Commun. 2022, 58, 12831–12834.
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-Identification of Small Molecules Inhibiting Cardiomyocyte Necrosis and Apoptosis by Autophagy Induction and Metabolism Reprogramming

D. Liu, F. Peyre, Y. A. Loissell-Baltazar, D. Courilleau, S. Lacas-Gervais, V. Nicolas, E. Jacquet, S. Dokudovskaya, F. Taran, J.-C. Cintrat, C. Brenner
Cells 2022, 10.3390/cells11030474 

- Late-stage carbon-14 labeling and isotope exchange: emerging opportunities and future challenges

V. Babin, F. Taran, D. Audisio* 
JACS Au, 2022, 2, 1234–1251

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- Comparison of the blood-brain barrier transport and vulnerability to P-glycoprotein-mediated drug-drug interaction of domperidone versus metoclopramide assessed using in vitro assay and PET imaging

L. Breuil, S. Goutal, S. Marie, A. Del Vecchio, D. Audisio, A. Soyer, M. Goislard, W. Saba, N. Tournier, F. Caillé 
Pharmaceutics 2022, 14, 1658

- Directed Palladium Catalyzed C–H (Ethoxycarbonyl)difluoromethylthiolation Reactions

F. Doche, J. Escudero, F. Petit-Cancelier, H.-Y. Xiong, S. Couve-Bonnaire, D. Audisio, T. Poisson, T. Besset 
Chem. Eur. J. 2022 e202202099.

- A sydnone-based route to indazolo[2,3-a]quinoxaline derivatives

M. Louis, A. Talbot, D. Lamaa, A. Sallustrau, D. Audisio, F. Taran*
SynLett 2022, 33, 791-794.

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- Monitoring in vivo performances of protein-drug conjugates using site-selective dual radiolabeling and ex vivo digital imaging

H. Cahuzac, A. Sallustrau, C. Malgorn, F. Beau, P. Barbe, V. Babin, S. Dubois, A. Palazzolo, R. Thai, I. Correia, K. Baek Lee, S. Garcia-Argote, O. Lequin, M. Keck, H. Nozach, S. Feuillastre, X. Ge, G. Pieters, D. Audisio, L. Devel 
J. Med Chem. 2022, 65, 6953–6968.

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- Parallel Screening with 14C-Labeled Carbon Dioxide: De-risking the Staudinger-Aza-Wittig Reaction 

V. Babin, A. Sallustrau, M. Molins, A. Labiche, A. Goudet, F. Taran, D. Audisio*
Eur. J. Org. Chem. 2022, e202200133.

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- Selective Chlorination of Iminosydnones for Fast Release of Amide, Sulfonamide and Urea-Containing Drugs

M. Feng, L. Madegard, M. Riomet, M. Louis, P. A. Champagne, G. Pieters, D. Audisio, F. Taran*
Chem. Commun. 2022. 58, 8500-8503 

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- Investigation on the stoichiometry of carbon dioxide in isotope exchange reactions with phenyl acetic acids 

A. Talbot, A. Sallustrau, A. Goudet, F. Taran, D. Audisio* 
SynLett 2022, 33, 171-176.
EuCheMS Young Investigators Workshop 2020 - SYNLETT Special Issue.

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2021



- Robust and General Procedure for Carbon Isotope Labeling of Linear Urea Derivatives with Carbon Dioxide

V. Babin, A. Sallustrau, O. Loreau, F. Caillé, A. Goudet, H. Cahuzac, A. Del Vecchio, F. Taran, D. Audisio*
Chem Commun, 2021, 57, 6680-6683

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- Detection of expanded-spectrum cephalosporin hydrolysis by lateral flow immunoassay

C. Moguet, C. Gonzalez, A. Sallustrau, S. Gelhaye, T. Naas, S. Simon, H. Volland
Microbial Biotechnology 2021, DOI: 10.1111/1751-7915.13892


- Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation

M. Feng, J. De Oliveira, A. Sallustrau, G. Destro, P. Thuéry, S. Roy, T. Cantat, C. S. Elmore, J. Blankenstein, F. Taran, D. Audisio*
J. Am. Chem. Soc. 2021, 143, 5659-5665

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- Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal

E. Yen-Pon, F. Buttard, L. Frédéric, P. Thuéry, F. Taran, G. Pieters, P. A. Champagne, D. Audisio*
JACS Au 2021, 1, 807-818

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- Click and Release Chemistry for Activity-based Purification of b-lactam targets

S. Saidjalolov, E. Braud, Z. Edoo, L. Iannazzo, F. Rusconi, M. Riomet, A. Sallustrau, F. Taran, M. Arthur, M. Fonvielle, M. Etheve-Quelquejeu
Chem. Eur. J. 2021, 27, 7687– 7695

- Photochemical Strategy for Carbon Isotope Exchange with CO2

V. Babin, A. Talbot, A. Labiche, G. Destro, A. Del Vecchio, C. S. Elmore, F. Taran, A. Sallustrau, D. Audisio*
ACS Catal. 2021, 11, 2968−2976

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- Click and Bio-Orthogonal Reactions with Mesoionic Compounds

K. Porte, M. Riomet, C. Figliola, D. Audisio, F. Taran*
Chem. Rev. 2021, 121, 6718-6743

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- Bioorthogonal Reactions in Animals
K. Porte, M. Riberaud, R. Chatre, D. Audisio, S. Papot,* F. Taran*
CHEMBIOCHEM 2021, 22, 100-113


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2020




- Carbon Isotope Labeling of Carbamates by Late-Stage [11C], [13C] and [14C] Carbon Dioxide Incorporation

A. Del Vecchio, A. Talbot, F. Caillé, A. Chevalier, A. Sallustrau, O. Loreau, G. Destro, F. Taran, D. Audisio*
Chem. Commun., 2020, 56, 11677-11680

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- Development of a Mass Spectrometry Imaging Method for Detecting and Mapping Graphene Oxide Nanoparticles in Rodent Tissues

H. Cazier, C. Malgorn, N. Fresneau, D. Georgin, A. Sallustrau, C. Chollet, J.-C. Tabet, S. Campidelli, M. Pinault, M. Mayne, F. Taran, V. Dive, C. Junot, F. Fenaille, B. Colsch
J. Am. Soc. Mass Spectrom. 2020, 31, 5, 1025–1036


- Fluorogenic iminosydnones: bioorthogonal tools for double turn-on click-and-release reactions

M. Riomet, K. Porte, A. Wijkhuisen, D. Audisio, F. Taran*
Chem Commun 2020, 56, 7183-7186

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- Transition-Metal-Free Carbon Isotope Exchange of Phenyl Acetic Acids

G. Destro, K. Horkka, O. Loreau, D.-A. Buisson, Lee Kingston, A. Del Vecchio, M. Schou, C. S. Elmore, F. Taran, T. Cantat, D. Audisio* 
Angew. Chem. Int. Ed. 2020, 59, 13490-13495

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- Fluorogenic probes based on polycyclic sydnone scaffolds

L. Plougastel, D. Lamaa, E. Yen-Pon, D. Audisio,* F. Taran*
Tetrahedron, 2020, 51, 131250
Invited contribution: special issue dedicated to Prof. Nuno Maulide

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- Access to N-Carbonyl Derivatives of Iminosydnones by Carbonylimidazolium Activation

M. Riomet,* K. Porte, L. Madegard, P. Thuéry, D. Audisio, F. Taran*
Org. Lett. 2020, 22, 6, 2403-2408

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- Nanotoxicology at the particle/micelle frontier: influence of core-polymerization on the intracellular distribution, cytotoxicity and genotoxicity of polydiacetylene micelles

F. Costamagna, H. Hillaireau, J. Vergnaud, D. Clarisse, L. Jamgotchian, O. Loreau, S. Denis, E. Gravel, E. Doris, E. Fattal
Nanoscale, 2020, 12, 2452-2463


- Automated linkage of proteins and payloads producing monodisperse conjugates

I. Dovgan, A. Hentz, O. Koniev, A. Ehkirch, S. Hessmann, S. Ursuegui, S. Delacroix, M. Riomet, F. Taran, S. Cianférani, S. Kolodych, A. Wagner
Chem. Sci. 2020, 11, 1210–1215

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2019




- Accelerated Discovery in Photocatalysis by a Combined Screening Approach Involving MS Tags

M. Teders, S. Bernard, K. Gottschalk, J. L. Schwarz, E. A. Standley, E. Decuypere, C. G. Daniliuc, D. Audisio, F. Taran,* F. Glorius*
Org. Lett. 2019, 21, 9747−9752

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- New fluorine-18 pretargeting PET imaging by bioorthogonal chlorosydnone–cycloalkyne click reaction 

M. Richard, C. Truillet, V. L. Tran, H. Liu, K. Porte, D. Audisio, M. Roche, B. Jego, S. Cholet, F. Fenaille, B. Kuhnast, F. Taran,* S. Specklin*
Chem. Commun., 2019, 55, 10400-10403

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- Visible-Light Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling

M. Sardana, J. Bergman, C. Ericsson, L. P. Kingston, M. Schou, C. Dugave, D. Audisio, C. S. Elmore
J. Org. Chem. 2019, 84, 16076−16085

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- Strain-Promoted 1,3-Dithiolium-4-olates/Alkyne Cycloaddition

R. Arun Kumar, M. R. Pattanayak, E. Yen-Pon, J. Elyian, K. Porte, S. Bernard, M. Riomet, P. Thuéry, D. Audisio,* F. Taran*
Angew. Chem. Int. Ed. 2019, 58, 14544-14548

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- Dodecyl creatine ester-loaded nanoemulsion as a promising therapy for creatine transporter deficiency

G. Ullio-Gamboa, K. C. Udobi, S. Dezard, M. K. Perna, K. N. Miles, N. Costa, F. Taran, A. Pruvost, J.-P. Benoit, M. R. Skelton, P. de Lonlay, A. Mabondzo 
Nanomedicine, 2019, 14, 1579–1593


- A Catalytic Decarboxylation/Carboxylation Platform for Accessing Isotopically-Labeled Carboxylic Acids

A. Tortajada Navarro, Y. Duan, B. Sahoo, F. Cong, G. Toupalas, A. Sallustrau, O. Loreau, D. Audisio, R. Martin*
ACS Catal. 2019, 9, 5897−5901

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- Controlled Release of a Micelle Payload via Sequential Enzymatic and Bioorthogonal Reactions in Living Systems

K. Porte, B. Renoux, E. Péraudeau, J. Clarhaut, B. Eddhif, P. Poinot, E. Gravel, E. Doris, A. Wijkhuisen, D. Audisio, S. Papot,* F. Taran*
Angew. Chem. Int. Ed. 2019, 58,6366 –6370

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- A FRET probe for the detection of alkylating agents

W. Tuo, J. Bouquet, F. Taran,* T. Le Gall*
Chem. Commun., 2019, 55, 8655-8658

- Sydnones-Based Turn-On Fluorogenic Probes for No-Wash Protein Labeling and in-Cell Imaging

L. Plougastel, M. Pattanayak,  M. Riomet, S. Bregant,  A. Sallustrau,  M. Nothisen, A. Wagner, D. Audisio, F. Taran*
Chem. Commun., 2019,55, 4582-4585 

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- Sydnone-based Approach to Hetero-helicenes Through 1,3-Dipolar-Cycloadditions

E. Yen-Pon, P. A. Champagne, L. Plougastel, S. Gabillet, P. Thuery, M. Johnson, G. Muller, G. Pieters, F. Taran, K. N. Houk, D. Audisio*
J. Am. Chem. Soc. 2019, 141, 1435–1440.

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- Dynamic Carbon Isotope Exchange of Pharmaceuticals with Labeled CO2

G. Destro, O. Loreau, E. Marcon, F. Taran, T. Cantat,* D. Audisio*
J. Am. Chem. Soc. 2019, 141, 780-784.

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2018




- Copper-Catalyzed Aza-Iminosydnone-Alkyne Cycloaddition Reaction Discovered by Screening

E. Decuypere, S. Bernard, M. Feng, K. Porte, M. Riomet, P. Thuery, D. Audisio, F. Taran*
ACS Catal. 2018, 8, 11882-11888

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- Sydnone-coumarins as clickable turn-on fluorescent sensors for molecular imaging

Elodie Decuypère, Margaux Riomet, Antoine Sallustrau, Sarah Bregant, Robert Thai, Grégory Pieters, Gilles Clavier, Davide Audisio, Frédéric Taran* 
Chem. Commun. 201854, 10758-10761

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- Late‐Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO2

Antonio Del Vecchio, Fabien Caillé, Arnaud Chevalier, Olivier Loreau, Kaisa Horkka, Christer Halldin, Magnus Schou, Nathalie Camus, Pascal Kessler, Bertrand Kuhnast, Frédéric Taran, Davide Audisio*
Angew. Chem. Int. Ed. 2018, 57, 7944 - 9748

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- Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes

Margaux Riomet, Elodie Decuypere, Karine Porte, Sabrina Bernard, Lucie Plougastel, Sergii Kolodych, Davide Audisio,* Frédéric Taran*
Chem. Eur. J. 2018, 24, 8535 – 8541


- Visible‐Light‐Driven Reduction of CO2 to CO and Its Subsequent Valorization in Carbonylation Chemistry and 13C Isotope Labeling

Philipp Gotico, Antonio Del Vecchio, Davide Audisio, Annamaria Quaranta, Zakaria Halime, Winfried Leibl, Ally Aukauloo
ChemPhotoChem 2018, 2, 715 - 719  (Cover Feature)

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- Recent Developments in Heterocycles Labeling with Carbon Isotopes

Antonio Del Vecchio, Gianluca Destro, Frédéric Taran, Davide Audisio*
J Label Compd Radiopharm. 201861, 988-1007



- A practical synthesis of valuable strained 8-membered ring derivatives for click chemistry

Sabrina Bernard, Ramar Arun Kumar, Karine Porte, Pierre Thuéry, Frédéric Taran, Davide Audisio* 
Eur. J. Org. Chem. 2018, 2000 - 2008


​2017




- Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

Sabrina Bernard, Davide Audisio, Margaux Riomet, Sarah Bregant, Antoine Sallustrau, Lucie Plougastel, Elodie Decuypere, Sandra Gabillet, Ramar Arun Kumar, Jijy Elyian, Minh Nguyet Trinh, Oleksandr Koniev, Alain Wagner, Sergii Kolodych,  Frédéric Taran*
Angew. Chem. Int. Ed. 2017, 56, 15612 –15616


- Sydnone–alkyne cycloaddition: applications in synthesis and bioconjugation

Elodie Decuypère, Lucie Plougastel, Davide Audisio, Frédéric Taran*
Chem. Commun., 2017, 53, 11515--11527


- Scalable and practical synthesis of clickable Cu-chelating azides

Antoine Sallustrau, Sarah Bregant,  Céline Chollet, Davide Audisio,* Frédéric Taran*
Chem. Commun., 2017, 53, 7890--7893


- A Synthetic Alternative to Canonical One-Carbon Metabolism

Madeleine Bouzon, Alain Perret, Olivier Loreau, Valerie Delmas, Nadia Perchat, Jean Weissenbach, Frédéric Taran, Philippe Marlierè*
ACS Synth. Biol. 2017, 6, 1520−1533

- Slow Phospholipid Exchange between a Detergent-Solubilized Membrane Protein and Lipid-Detergent Mixed Micelles: Brominated Phospholipids as Tools to Follow Its Kinetics

Cédric Montigny*, Thibaud Dieudonné, Steéphane Orlowski, José Luis Vàzquez-Ibar, Carole Gauron, Dominique Georgin, Sten Lund, Marc le Maire, Jesper V. Møller, Philippe Champeil, Guillaume Lenoir*

PLOS ONE, 2017, DOI:10.1371/journal.pone.0170481

2016




- Ultrafast Click Chemistry with Fluorosydnones

Hui Liu, Davide Audisio, Lucie Plougastel, Elodie Decuypère, David-Alexandre Buisson, Oleksandr Koniev, Sergii Kolodych, Alain Wagner, Mourad Elhabiri, Anna Krzyczmonik, Sarita Forsback, Olof Solin, Véronique Gouverneur, and Frédéric Taran*

Angew. Chem. Int. Ed. 2016, 55, 12073 –12077


- The Multiple Facets of Iodine(III) Compounds in an Unprecedented Catalytic Auto-amination for Chiral Amine Synthesis

Julien Buendia, Gwendal Grelier, Benjamin Darses, Amanda G. Jarvis, Frédéric Taran, and Philippe Dauban*
Angew. Chem. Int. Ed. 2016, 55, 7530 –7533

- A Straightforward Access to [14C]- and [13C]-Labeled 2-Aminobenzoxazoles and Benzothiazoles via a KCN Polarity Inversion Strategy

Olivier Loreau, Nathalie Camus, Frédéric Taran, Davide Audisio*
Synlett, 2016, 27 (12), 1798-1802


- e-EROS Encyclopedia of Reagents for Organic Synthesis:  "tert-Butyl Nitrite" 

Davide Audisio, Frédéric Taran
DOI: 10.1002/047084289X.rn01922

2015




- Enzyme immunoassays as screening tools for catalysts and reaction discovery

Chrostophe Creminon, Frédéric Taran*
Chem. Commun. 2016, 51, 7996-8009

- Copper(I)-catalyzed cycloaddition of 4-bromosydnones and alkynes for the regioselective synthesis of 1,4,5-trisubstituted pyrazoles

Elodie Decuypere, Simon Specklin, Sandra Gabillet, Davide Audisio, Hui Liu, Lucie Plougastel, Sergii Kolodych, Frédéric Taran 
Org. Lett. 2015, 17, 362-365, 2015

- Palladium-catalyzed decarboxylative cyanation of aromatic carboxylic acids using [13C] and [14C]-KCN

Olivier Loreau, Dominique Georgin, Frédéric Taran, Davide Audisio*
J. Label. Compd. Radiopharm. 2015,58, 425-428

- A screening method of uranyl extractants in H2SO4 solutions

Pasquier S, Vercouter T,* Taran F, Lamouroux C, Plancque G, Berthet JC
Tetrahedron Lett. 2015, 56, 308-311

- Dodecyl creatine ester and lipid nanocapsule: a double strategy for the treatment of creatine transporter deficiency

Alexandra Trotier-Faurion, Catherine Passirani, Jérôme Béjaud, Sophie Dézard, Vassili Valayannopoulos, Fréderic Taran, Pascale de Lonlay, Jean-Pierre Benoit, Aloïse Mabondzo*
Nanomedicine, 2015, 10, 185-191

2014




- Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media

Bevilacqua Valentina, King Mathias, Chaumontet Manon, Nothisen Marc, Gabillet Sandra, Buisson David, Puente Céline, Wagner Alain, Taran Fédéric*
Angew. Chem. Int. Ed. 2014, 53, 5872-5876

- Carbon Nanotube Trans location to Distant Organs after Pulmonary Exposure: Insights from in Situ 14C-Radiolabeling and Tissue Radioimaging

Bertrand Czarny, Dominique Georgin, Fannely Berthon, Gael Plastow, Mathieu Pinault, Gilles Patriarche, Aurélie Thuleau, Martine Mayne L'Hermite, Frédéric Taran, Vincent Dive*
ACS NANO, 2014, 8, 5715-5724

- A Phosphine-Catalyzed Preparation of 4-Arylidene-5-imidazolones

Sandra Gabillet, Olivier Loreau, Simon Specklin, Evelia Rasalofonjatovo, Frédéric Taran*
J. Org. Chem. 2014, 79, 9894-9898

- 4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

Lucie Plougastel, Olekandr Koniev, Simon Specklin, Elodie Decuypère, Christophe Creminon, David A. Buisson, Alain Wagner, Sergii Kolodych, Frédéric Taran*
Chem. Commun. 2014, 50, 9376-9378

- One-Pot Synthesis of 1,4-Disubstituted Pyrazoles from Arylglycines via Copper-Catalyzed Sydnone-Alkyne Cycloaddition Reaction

Simon Specklin, Elodie Decuypère, Lucie Plougastel, Soifia Aliani, Frédéric Taran*
J. Org. Chem. 2014, 79, 7772-7777

- Smart Detection of Toxic Metal Ions, Pb2+ and Cd2+, Using a 129Xe NMR-Based Sensor

Nawal Tassali, Naoko Kotera, Céline Boutin, Estelle Léonce, Yves Boulard, Bernard Rousseau*, Emmanuelle Dubost, Frédéric Taran, Thierry Brotin, Jean-Pierre Dutasta, Patrick Berthault*
Anal. Chem. 2014, 86, 1783-1788