FLow chemistry for Isotopic eXchange

Deliverables

New efficient and safer isotopic sources usable for 1H2H 12C13C and 14N15N isotope exchange in the FLIXBOX environment with an assessment in terms of efficiency and safety relative to standard isotope sources

New (immobilzed) homogeneous catalysts (final)

New (immobilzed) homogeneous catalysts working for continuous flow 1H/2H, 12C/13C and 14N/15N isotope exchange. Efficiency and robustness screenings.

Updated Risk Management Plan (RP2)

Updated Risk Management Plan based on previous results experience and encountered issues according to SB decisions and AB remarks avise and suggestions

Innovative isotopic sources (initial)

New efficient and safer isotopic exchange for 1H/2H and 12C/13C isotope exchange which can be used either for batch and flow chemistry and are consistent with a specific and selective isotopic exchange.

New nanoparticle catalysts for isotopic exchange (initial)

New nanoparticle catalysts (initial) for batch/flow 1H/2H and 12C/13C exchange with high specificities and selectivities. Thes catalysts are decorated nanopartcles which can also be adsorbed on different supports (see heterogeneous catalysts).

Dissemination and exploitation (RP2)

The dissemination and exploitation plan (RP2) based on expected results after assesment of preliminary data will be reevaluated and regularly updated in order to maximize the impact of consolidated project results and outputs.

Basic modules for flow 1H/2H exchange

"Basic modules for flow 1H/2H exchange containing either commercial or ""standard"" catalysts already used by partners. They will be used as a proof of concept of the FLIX-CAT paradigm. "

Basic modules for flow 12C/13C exchange

"Basic modules for flow 12C/13C exchange containing either commercial or ""standard"" catalysts already used by partners. hey will be used as a proof of concept of the FLIX-CAT paradigm. "

M2 Meeting

M2 Meeting report including agenda list of participants minutes pictures ERs and ESRs presentations AB remarks and decisions taken during this consortium meeting This document will serve as proof and guidelines for implementation of decisions made by the SB

M1 Meeting

M1 Meeting report including agenda list of participants minutes pictures ERs and ESRs presentations AB remarks and decisions taken during this consortium meeting This document will serve as proof and guidelines for implementation of decisions made by the SB

New nanoparticle catalysts for isotope exchange (final)

New metal nanoparticle catalysts usable for continuous flow 1H2H 12C13C and 14N15N isotope exchange selected on the basis of robustness tests efficiency specificity selectivity metal leaching catalyst resistance and compatibility with flow chemistry conditions and process

Dissemination and exploitation (RP3)

The dissemination and exploitation plan (RP3) based on final project results will be produced in order to maximize the impact of the project outputs.

New heterogeneous catalysts (final)

New heteogeneous ( mainly nanoparticles on support) catalysts for continous flow 1H/2H, 12C,13C and 14N/15N isotope exchange in the FLIX-BOX environment with an assessment of efficiency, specificity and selectivity.

M3 Meeting

M3 Meeting report including agenda, list of participants, minutes, pictures, ERs and ESRs presentations, AB remarks and decisions taken during this consortium meeting. This document will serve as proof and guidelines for implementation of decisions made by the SB.

Website and Logo

Information about project website, logo and communication accounts (Twitter page, etc.).

Publications

Nanocatalyzed Hydrogen Isotope Exchange

Author(s): Marco Lepron, Marion Daniel-Bertrand, Gabriel Mencia, Bruno Chaudret, Sophie Feuillastre, Grégory Pieters
Published in: Accounts of Chemical Research, 2021, ISSN 0001-4842
Publisher: American Chemical Society
DOI: 10.1021/acs.accounts.0c00721

A Nickel(II)‐Mediated Thiocarbonylation Strategy for Carbon Isotope Labeling of Aliphatic Carboxamides

Author(s): Simon S. Pedersen; Aske S. Donslund; Jesper H. Mikkelsen; Oskar S. Bakholm; Florian Papp; Kim B. Jensen; Magnus B. F. Gustafsson; Troels Skrydstrup
Published in: Chemistry – A European Journal, Issue 27, 2021, ISSN 0000-0000
Publisher: _
DOI: 10.1002/chem.202005261

Recent Developments for the Deuterium and Tritium Labeling of Organic Molecules

Author(s): Sara Kopf; Florian Bourriquen; Wu Li; Helfried Neumann; Kathrin Junge; Matthias Beller
Published in: Chemical Reviews, Issue 1, 2022, ISSN 1520-6890
Publisher: Chemical Review
DOI: 10.1021/acs.chemrev.1c00795

Photochemical Strategy for Carbon Isotope Exchange with CO 2

Author(s): Victor Babin, Alex Talbot, Alexandre Labiche, Gianluca Destro, Antonio Del Vecchio, Charles S. Elmore, Frédéric Taran, Antoine Sallustrau, Davide Audisio
Published in: ACS Catalysis, Issue 11/5, 2021, Page(s) 2968-2976, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.0c05344

Supramolecular nanocapsules as two-fold stabilizers of outer-cavity sub-nanometric Ru NPs and inner-cavity ultra-small Ru clusters

Author(s): Ernest Ubasart, Irene Mustieles Marin, Juan Manuel Asensio, Gabriel Mencia, Ángela M. López-Vinasco, Cristina García-Simón, Iker del Rosal, Romuald Poteau, Bruno Chaudret, Xavi Ribas
Published in: Nanoscale Horizon, 2022, ISSN 0000-0000
Publisher: _
DOI: 10.1039/d1nh00677k

Late-Stage Carbon-14 Labeling and Isotope Exchange: Emerging Opportunities and Future Challenges

Author(s): Victor Babin; Frédéric Taran; Davide Audisio
Published in: Jacs Au, Issue 11, 2022, ISSN 1520-5126
Publisher: _
DOI: 10.1021/jacsau.2c00030

Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates

Author(s): Stephanie J. Ton, Anne K. Ravn, Daniel V. Hoffmann, Craig Day, Lee Kingston, Charles S. Elmore, Troels Skrydstrup
Published in: JACS Au, Issue 3, 2023, ISSN 0000-0000
Publisher: American Chemical Society
DOI: 10.1021/jacsau.2c00708

Manganese‐Catalysed Deuterium Labelling of Anilines and Electron‐Rich (Hetero)Arenes

Author(s): Florian Bourriquen; Nils Rockstroh; Stephan Bartling; Kathrin Junge; Matthias Beller
Published in: Wiley Online Library, Issue 9, 2021, ISSN 1359-7345
Publisher: Royal Society of Chemistry
DOI: 10.1002/anie.202202423

Raney Nickel-Catalyzed Deuterium Labeling of Nitrogen-Containing Heterocycles and Pharmaceuticals under Continuous Flow Conditions

Author(s): Ferenc Minya, Ádám Mészáros, Eszter Csizmadia, Dávid Suskó, Mounir Raji, Gellért Sipos
Published in: Advanced Synthesis & Catalysis, 2024, ISSN 0000-0000
Publisher: _
DOI: 10.1002/adsc.202400168

Parallel Screening with <sup>14</sup> C‐Labeled Carbon Dioxide: De‐risking the Staudinger‐Aza‐Wittig Reaction**

Author(s): Victor Babin; Antoine Sallustrau; Maxime Molins; Alexandre Labiche; Amélie Goudet; Frédéric Taran; Davide Audisio
Published in: European Journal of Organic Chemistry, Issue 6, 2022, ISSN 0000-0000
Publisher: _
DOI: 10.1002/ejoc.202200133

Photocatalytic Functionalization of Dehydroalanine‐Derived Peptides in Batch and Flow

Author(s): Nikolaos Kaplaneris, Merve Akdeniz, Méritxell Fillols, Francesca Arrighi, Fabian Raymenants, Gana Sanil, Daniel T Gryko, Timothy Noël
Published in: Angewandte Chemie, 2024, ISSN 0000-0000
Publisher: Wiley
DOI: 10.1002/anie.202403271

C(sp3)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow

Author(s): Dmitrii Nagornîi, Fabian Raymenants, Nikolaos Kaplaneris, Timothy Noël
Published in: Nature Communications, Issue 15/1, 2024, ISSN 0000-0000
Publisher: _
DOI: 10.1038/s41467-024-49322-w

Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation

Author(s): Minghao Feng; Joao De Oliveira; Antoine Sallustrau; Gianluca Destro; Pierre Thuéry; Sebastien Roy; Thibault Cantat; Charles S. Elmore; Jorg Blankenstein; Frédéric Taran; Davide Audisio
Published in: Journal of the American Chemical Society, Issue 15, 2021, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c01923

N-Heterocyclic Carbene-Based Iridium and Ruthenium/Iridium Nanoparticles for the Hydrogen Isotope Exchange Reaction through C-H Bond Activations

Author(s): Alejandra Zuluaga-Villamil, Gabriel Mencia, Juan M. Asensio, Pier-Francesco Fazzini, Edwin A. Baquero, Bruno Chaudret
Published in: Organometallics, 2022, ISSN 0000-0000
Publisher: _
DOI: 10.1021/acs.organomet.2c00288

Dual role of benzophenone enables a fast and scalable C-4 selective alkylation of pyridines in flow

Author(s): Jesús Sanjosé-Orduna; Rodrigo C. Silva; Fabian Raymenants; Bente Reus; Jannik Thaens; Kleber T. de Oliveira; Timothy Noël
Published in: Chemical Science, Issue 4, 2022, ISSN 2041-6539
Publisher: Chemical Science
DOI: 10.1039/d2sc04990b

Easy-to-Implement Hydrogen Isotope Exchange for the Labeling of <i>N</i>-Heterocycles, Alkylkamines, Benzylic Scaffolds, and Pharmaceuticals

Author(s): Etienne Levernier; Kevin Tatoueix; Sébastien Garcia-Argote; Viktor Pfeifer; Ralf Kiesling; Edmond Gravel; Sophie Feuillastre; Grégory Pieters
Published in: Journal access of the American Chemical Society, Issue 2, 2022, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacsau.1c00503

Efficient palladium-catalyzed electrocarboxylation enables late-stage carbon isotope labelling

Author(s): Gabriel M. F. Batista, Ruth Ebenbauer, Craig Day, Jonas Bergare, Karoline T. Neumann, Kathrin H. Hopmann, Charles S. Elmore, Alonso Rosas-Hernandez, Troels Skrydstrup
Published in: Nature Communications, Issue 15, 2024, ISSN 0000-0000
Publisher: _
DOI: 10.1038/s41467-024-46820-9

Lignocellulose Conversion via Catalytic Transformations Yields Methoxyterephthalic Acid Directly from Sawdust

Author(s): Simon Pedersen; Gabriel Batista; Martin Henriksen; Hans Christian Hammershøj; Kathrin Hopmann; Troels Skrydstrup
Published in: JACS Au, Issue 3, 2023, ISSN 0000-0000
Publisher: American Chemical Society
DOI: 10.1021/jacsau.3c00092

Low Pressure Carbonylation of Benzyl Carbonates and Carbamates for Applications in 13C Isotope Labeling and Catalytic CO2 Reduction

Author(s): Craig S. Day, Stephanie J. Ton, Clemens Kaussler, Daniel V. Hoffmann, Troels Skrydstrup
Published in: Angewandte Chemie International Edition, Issue 62, 2023, ISSN 0000-0000
Publisher: Wiley-VCH
DOI: 10.1002/anie.202308238

Manganese-catalyzed selective C–H activation and deuteration by means of a catalytic transient directing group strategy

Author(s): Sara Kopf, Helfried Neumann, Matthias Beller
Published in: Chemical Communications, Issue 57/9, 2021, Page(s) 1137-1140, ISSN 1359-7345
Publisher: Royal Society of Chemistry
DOI: 10.1039/d0cc07675a

Ruthenium-Catalyzed Deuteration of Aromatic Carbonyl Compounds with a Catalytic Transient Directing Group.

Author(s): Sara Kopf; Fei Ye; Fei Ye; Helfried Neumann; Matthias Beller
Published in: Chemistry, Issue 2, 2021, ISSN 1521-3765
Publisher: Wiley VCH
DOI: 10.1002/chem.202100468

Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement.

Author(s): Stephanie J. Ton; Karoline T. Neumann; Peter Nørby; Troels Skrydstrup
Published in: Journal of the American Chemical Society, Issue 143, 2021, ISSN 0000-0000
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c09170

Catalytic disconnection of C-O bonds in epoxy resins and composites

Author(s): Alexander Ahrens, Andreas Bonde, Hongwei Sun, Nina Køln Wittig, Hans Christian D. Hammershøj, Gabriel M. F. Batista, Andreas Sommerfeldt, Simon Frølich, Henrik Birkedal, Troels Skrydstrup
Published in: Nature, Issue 617, 2023, ISSN 0000-0000
Publisher: _
DOI: 10.1038/s41586-023-05944-6

In situ Generated Iridium Nanoparticles as Hydride Donors in Photoredox-Catalyzed Hydrogen Isotope Exchange Reactions with Deuterium and Tritium Gas

Author(s): Henrik Kramp, Remo Weck, Martin Sandvoss, Anna Sib, Gabriel Mencia, Pier-Francesco Fazzini, Bruno Chaudret, Volker Derdau
Published in: Angewandte Chemie, 2023, ISSN 0000-0000
Publisher: Wiley-VCH
DOI: 10.1002/anie.202308983

Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides

Author(s): Wu Li; Ruiyang Qu; Weiping Liu; Florian Bourriquen; Stephan Bartling; Nils Rockstroh; Kathrin Junge; Matthias Beller
Published in: Chemical Science, Issue 10, 2021, ISSN 2041-6520
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1sc04259a

Water-soluble NHC Pd/Ni bimetallic nanoparticles for H/D exchange in aromatic amino-acids

Author(s): Oscar Suárez-Riaño, Gabriel Mencia, Simon Tricard, Jerome Esvan, Pier-Francesco Fazzini, Bruno Chaudret and Edwin A. Baquero
Published in: Chem. Comm., 2023, ISSN 0000-0000
Publisher: _
DOI: 10.1039/d2cc06019a

Exploring the Parameters Controlling Product Selectivity in Electrochemical CO2 Reduction in Competition with Hydrogen Evolution Employing Manganese Bipyridine Complexes

Author(s): Wanwan Hong, Mahika Luthra, Joakim B. Jakobsen, Monica R: Madsen, Abril C. Castro, Hans Christian D. Hammershøj, Steen U. Pedersen, David Balcells, Troels Skrydstrup, Kim Daasbjerg, Ainara Nova
Published in: ACS Catalysis, Issue 13, 2023, ISSN 0000-0000
Publisher: _
DOI: 10.1021/acscatal.2c05951

Base‐Mediated Remote Deuteration of N ‐Heteroarenes – Broad Scope and Mechanism

Author(s): Sara Kopf; Jiali Liu; Robert Franke; Haijun Jiao; Helfried Neumann; Matthias Beller
Published in: European Journal of Organic Chemistry, Issue 4, 2022, ISSN 0947-6539
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/ejoc.202200204

Multi-carbon labelling of active pharmaceutical ingredients enabled by a three-gas surrogate hydroformylation

Author(s): Hans Christian D. Hammershøj, Haraldur G. Gudmundsson, Samuel Kjærsgaard, Jonas Bønnelykke, Julia Kolodiazhnaia, Troels Skrydstrup
Published in: Nature Synthesis, Issue 2, 2023, ISSN 0000-0000
Publisher: _
DOI: 10.1038/s44160-022-00223-0

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

Author(s): Victor Babin, Antoine Sallustrau, Olivier Loreau, Fabien Caillé, Amélie Gouder, Héloïse Cahuzac, Antinio Del Vecchio, Frédéric Taran, Davide Audisio
Published in: Organic Chemistry (ChemRxiv.2021), 2021, ISSN 0000-0000
Publisher: _
DOI: 10.1039/d1cc02665h

Deliverables

Publications

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