laboratoire de Réactivité et Catalyse Organique (RCO)
Presentation
Laboratory of Reactivity and Organic Catalysis (RCO, Professor Guillaume Berionni)
Our group's research interests range over a variety of topics within the fields of organometallic, main-group and physical organic chemistry.
Our current research focuses on the development of structurally unique nitrogen- and phosphorus containing Lewis bases and new carbon- and boron-containing Lewis acids.
We investigate their reactivity and properties, and then combine them in pairs for creating new bifunctional acid–base catalysts. Creating new chemical entities based on main-group elements to mimic the rich and multifaceted chemistry of transition-metal complexes is an exciting challenge and requires a combination of state-of-the-art synthetic and computational chemistry.
The reactivities of these metallomimetic molecular systems are investigated quantitatively by kinetics and thermodynamic measurements which allows the subsequent fine-tuning and optimization of their structures and their efficient implementations in new chemical processes (hydrogenation reactions, CH borylation reactions, small molecules activation).
The development of ground-breaking main-group catalysts based on the most abundant elements in the earth crust will have a wide impact on chemical energy transformation and storage, as well as on bulk and fine chemical synthesis.
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May 2021 From left to right : Guillaume Berionni - Ali Ben Saida - Alain Krief - Mathieu Gama - Damien Mahaut - Arnaud Osi - Aurélien Chardon - Thu-Hong Doan - Dorothée Brandt - Jennifer Theissen - Esteban Danloy - Antoine Willems |
Funding Agencies
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The group is funded since 2018 by the Belgian National Fund for Scientific Research (Fonds National de la Recherche Scientifique FNRS)
Since 2022 the group is funded by the European Research Council (ERC) under the Horizon Europe research and innovation programme
Within the context of an ARC inter-university collaboration with the UCLouvain University, the group is supported by the Fédération Wallonie-Bruxelles funds for fundamental research, through its ‘Actions de Recherche Concertées’ (ARC, Collective Research Initiatives) programme.
Prof. Guillaume Berionni (Namur Institute of Structured Matter - University of Namur) has been recently awarded an ERC consolidator grant.
With this funding instrument, the European Research Council enables outstanding scientists to implement pioneering concepts over a period of five years and thus strengthens the European research landscape.
The ERC received 2652 consolidator grant proposals, and a total of 313 laureates were funded in Europa. In the physical sciences and engineering PE5 panel (Synthetic Chemistry and Materials), a total of 12 ERC CoG grants were awarded this year in Europa, among which only one (this project B-YOND) was awarded in Belgium. ERC Consolidator Grants are designed to support excellent research programs which must demonstrate ground-breaking nature and multidisciplinary ambition.
Inspired by transition-metal catalysis and main-group chemistry, the recently funded ERC project “B-yond” aims at reprograming molecular systems based on s and p block elements to overstep current chemistry reactivity rules.
A milestone of this project is the formulation of acids and bases with minimal reorganization energies suitable for promoting new catalytic processes. The development of ground-breaking main-group catalysts based on the most abundant elements in the earth crust will have a wide impact on chemical materials transformation, as well as on bulk and fine chemical synthesis.
The research outcomes will lay the basis for developing new energy and resources management strategies, notably through novel approaches to catalysts design and sustainable materials development, by avoiding the use of precious transition-metal elements.
Thus, the research project B-YOND addresses important challenges in the quest for a sustainable future, since Berionni and his working group will develop new reactive species and catalysts that benefit a variety of chemical technologies.
Additional links:
- Prof. Berionni research group website: Laboratory of Reactivity and Organic Catalysis
- A recent interview of Prof. Berionni: Young Career Focus presents Guillaume Berionni, Synform (Thieme Chemistry, 2021).
- A recent highlight (Namur Institute of Structured Mater, 2022) on the applications of new pyramidal Lewis acids developed in the Berionni group: here
- A description of a former research program supported by the Belgian National Fund for Scientific Research (Fonds National de la Recherche Scientifique FNRS): here
- Link to the ERC consolidator grant webpage: here
Publications
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Regioselective Transition-Metal Free Arenes C-H Borylations: From Directing Groups to Borylation Template Reagents, G. Berionni, Angew. Chem. Int. Ed. 2022, 61, e202210284. [Download]
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Reprogramming Main-Group Compounds: Toward New Superelectrophilic and Superacidic Catalysts, G. Berionni, Chimie Nouvelle, 2022, 139, 27-29. DOI: 10.52809/cn2022.nxmn2068 [download]
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52
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A Selenium Substituted Pyramidal 9-Boratriptycene Lewis Acid, A. Osi, N. Tumanov, J. Wouters, A. Chardon, G. Berionni, Synthesis 2022, online, DOI: 10.1055/a-1840-5680. [download]
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9-phosphatriptycene derivatives: from their weak basicity to their application in frustrated Lewis pair chemistry D. Mahaut, G. Berionni, B. Champagne, J. Phys. Chem. A 2022, 126, 18, 2794–2801 [download] |
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50
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Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes D. Mahaut, B. Champagne, G. Berionni, 2022, ChemCatChem 2022,14, e202200294. [download] |
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Taming the Lewis Superacidity of Non-Planar Boranes: C-H Bond Activation and Non-Classical Binding Modes at Boron A. Osi, D. Mahaut, N. Tumanov, L. Fusaro, J. Wouters, B. Champagne, A. Chardon, G. Berionni. Angew. Chem. Int. Ed. 2022, 61, e202112342. [download] |
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48
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Young Career Focus presents Guillaume Berionni, Synform, 2021, 159-161 [download] |
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Future Prospects in Boron Chemistry: Boron Lewis Acids in Perspective Chem. Syn. 2021, 1:10. DOI: 10.20517/cs.2021.11 [download]
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46
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Rational Development of a Metal-Free Bifunctional System for the C-H Activation of Methane: A Density Functional Theory Investigation D. Mahaut, A. Chardon, L. Mineur, G. Berionni, B. Champagne, ChemPhysChem 2021, 22, 1958–1966.[download] |
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45
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Six-membered Rings with One Phosphorus Atom F. Rammal, V. Magné, G. Berionni, S. Lakhdar, Comprehensive Heterocyclic Chemistry IV, Elsevier, 2022, Volume 7, 685-717 (book chapter). [download] |
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44
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Four-membered Rings with One Phosphorus, Arsenic, Antimony, or Bismuth Atom V. Magné, F. Rammal, G. Berionni, S. Lakhdar, Comprehensive Heterocyclic Chemistry IV, Elsevier, 2022, Volume 2, 335-362 (book chapter). [download]
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43
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Sterically hindered ortho-substituted phosphatriptycenes as configurationally stable P-chirogenic triarylphosphines L. Hu, D. Mahaut, N. Tumanov, J. Wouters, L. Collard, R. Robiette, G. Berionni, Dalton Trans. 2021, 50, 4772-4777 [download] |
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42
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Triptycene Boronates, Boranes, and Boron Ate‐Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates M. Gama, X. Antognini Silva, T-H. Doan, A. Osi, A. Chardon, N. Tumanov, J. Wouters, G. Berionni, Eur. J. Org. Chem. 2021, 1440–1445 [download] |
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41
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Methylene Bridging Effect on the Structures, Lewis Acidities and Optical Properties of Semi Planar Triarylboranes T.-H. Doan, A. Chardon, A. Osi, D. Mahaut, N. Tumanov, J. Wouters, B. Champagne, G. Berionni, Chem. Eur. J. 2021, 27, 1736-1743. [download] |
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Non-planar Boron Lewis Acids Taking the Next Step: Development of Tunable Lewis Acids, Lewis Superacids and Bifunctional Catalysts A. Chardon, A. Osi, D. Mahaut, A. Ben Saida, G Berionni, Synlett. 2020, 31, 1639-1648. [download] |
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Controlled Generation of 9-Boratriptycene by Lewis Adduct Dissociation: Accessing a Unique Non-Planar Triarylborane A. Chardon, A. Osi, D. Mahaut, T.-H. Doan, N. Tumanov, J. Wouters, L. Fusaro, B. Champagne, G Berionni, Angew. Chem. Int. Ed. 2020, 59, 12402-12406. [download] |
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38
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Pushing the Lewis Acidity Boundaries of Boron Compounds With Non-Planar Triarylboranes Derived from Triptycenes A. Ben Saida, A. Chardon, A. Osi, N. Tumanov, J. Wouters, A. I. Adjieufack, B. Champagne, G. Berionni, Angew. Chem. Int. Ed. 2019, 58, 16889–16893. [download]
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37
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Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure–Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids L. Hu, D. Mahaut, N. Tumanov, J. Wouters, R. Robiette, G. Berionni, J. Org. Chem. 2019, 84, 11268−11274. [download]
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The Halogen–Samarium Exchange Reaction: Synthetic Applications and Kinetics L. Anthore‐Dalion, A. D. Benischke, B. Wei, G Berionni, P. Knochel, Angew. Chem. Int. Ed. 2019, 58, 4046. [download]
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Opening Up New Research Lines in Lewis Acid/Base Catalysis G. Berionni, L. Hu, A. Ben Saida, A. Chardon, M. Gama, A. Osi, D. Mahaut, X. Antognini Silva, Chimie Nouvelle, 2018, 128, 13. [download]
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Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles
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Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles C. García-Ruiz, J. L.-Y. Chen, C. Sandford, K. Feeney, G. Berionni, H. Mayr, V. K. Aggarwal, J. Am. Chem. Soc., 2017, 139, 15324-15327. [download] |
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Mechanistic studies of formal thioboration reactions of alkynes |
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Barbier continuous flow preparation and reactions of carbamoyllithiums for nucleophilic amidation M. A. Ganiek, M. R. Becker, G. Berionni, H. Zipse, P. Knochel*, Chem. Eur. J. 2017, 23, 10280-10284. [download] |
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Nucleophilicities and Lewis basicities of sterically hindered pyridines E. Follet, H. Zipse, S. Lakhdar, A. R. Ofial, G. Berionni*, Synthesis 2017, 49, 3495-3504. [special issue on the occasion of the 70th birthday of Professor Herbert Mayr] [download] |
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Superelectrophilicity in Michael-Type Reactions: Water Addition to 4-Nitrobenzodifuroxan S. Lakhdar,* G. Berionni*, F. Terrier,* Synthesis 2017, 49, 3453-3459. [special issue on the occasion of the 70th birthday of Professor Herbert Mayr] [download] |
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Reactivity-tuning in frustrated Lewis pairs: nucleophilicities and lewis basicities of sterically hindered phosphines E. Follet, P. Mayer, D. S. Stephenson, A. R. Ofial, G. Berionni*, Chem. Eur. J. 2017, 23, 7422-7427. [download] |
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Structures, Lewis acidities, electrophilicities, and protecting group abilities of phenyl-fluorenylium and tritylium ions. E. Follet, P. Mayer, G. Berionni*, Chem. Eur. J. 2017, 23, 623-630. [download][Selected as hot paper] |
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Nucleophilicity of alkyl zirconocene and titanocene precatalysts and kinetics of activation by carbenium ions and by B(C6F5)3. G. Berionni*, H. Kurouchi, L. Eisenburger, H. Mayr, Chem. Eur. J. 2016, 22, 11196-11200. [download] |
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Scope and mechanisms of frustrated Lewis pair catalyzed hydrogenation reactions of electron-deficient C=C double bonds V. Morozova, P. Mayer, G. Berionni*, Angew. Chem. Int. Ed. 2015, 54, 14508-14512. [download] |
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Structure and Reactivity of Indolyl-methylium Ions: Scope and Limitations in Synthetic Applications E. Follet, G. Berionni, P. Mayer, H. Mayr, J. Org. Chem. 2015, 80, 8643-8656. [download] |
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Structure and Reactivity of Boron-Ate Complexes Derived from Primary and Secondary Boronic Esters K. Feeney, G. Berionni, H. Mayr, V. K. Aggarwal, Org. Lett. 2015, 17, 2614-2617. [download] |
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Fine-Tuning of the Nucleophilic Reactivities of Boron-Ate Complexes Derived From Aryl and Heteroaryl Boronic Esters G. Berionni, A. I. Leonov, P. Mayer, A. R. Ofial, H. Mayr, Angew. Chem. Int. Ed. 2015, 54, 2780-2783. [download] |
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Stereoselective Synthesis and Reactions of Secondary Alkyllithium Reagents Functionalized at the 3-Position K. Moriya, D. Didier, M. Simon, J. M. Hammann, G. Berionni, K. Karaghiosoff, H. Zipse, H. Mayr, P. Knochel, Angew. Chem. Int. Ed. 2015, 54, 2754-2757. [download] |
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Aromaticity evaluations of planar [6]radialenes Guillaume Berionni*, Judy I. Chia Wu, Paul v R. Schleyer, Org. Lett. 2014, 16, 6116-6119 [download] |
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Di- and Triarylmethylium Ions as Probes for the Ambident Reactivities of Carbanions Derived from 5-Benzylated Meldrum's Acid X. Chen, Y. Tan, G. Berionni, A. R. Ofial, H. Mayr, Chem. Eur. J. 2014, 20, 11069-11077. [download] |
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New In Situ Trapping Metalations of Functionalized Arenes and Heteroarenes with TMPLi in the Presence of ZnCl2 and Other Metal Salts A. Frischmuth, M. Fernández, N. M. Barl, F. Achrainer, H. Zipse, G. Berionni, H. Mayr, K. Karaghiosoff, P. Knochel, Angew. Chem. Int. Ed. 2014, 53, 7928-7932. [download] |
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Mechanistic studies and quantification of the electrophilicity of aromatic triflones in sigma-complexation and SNAr reactions N. El Guesmi, G. Berionni, B.H Asghar, J. Fluorine. Chem. 2014, 160, 41-47 [download] |
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Diastereoselective Synthesis of Open-Chain Secondary Alkyllithium Compounds and Trapping Reactions with Electrophiles
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Electronic and solvent effects on kinetics of SNAr substitution reactions of substituted anilines with 2,6-bis(trifluoromethanesulfonyl)-4-nitroanisole N. El Guesmi, G. Berionni, B.H Asghar, Monatsh. Chemie (Chemical Monthly) 2013, 144, 1537-1545. [download] |
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Electrophilic Aromatic Substitutions of Aryltrifluoroborates with Retention of the BF3- Group: Quantification of the Activating and Directing Effects of the Trifluoroborate Group G. Berionni, V. Morozova, M. Heininger, P. Mayer, P. Knochel, H. Mayr, J. Am. Chem. Soc. 2013, 135, 6317-6324. [download][Highlighted in Synfact, 2013, 9, 723] |
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Nucleophilicity parameters for designing transition metal-free C-C bond forming reactions of organoboron compounds G. Berionni, B. Maji, P. Knochel, H. Mayr, Chem. Sci. 2012, 3, 878-882. [download][Highlighted in the blog of the RSC] |
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Synthesis and Reactivity of Highly Nucleophilic Pyridines N. De Rycke, G. Berionni, F. Couty, H. Mayr, R. Goumont, O. R. P. David, Org. Lett. 2011, 13, 530-533. [download][Highly cited paper] |
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The N-Alkylation of Substituted 4-Tetrazolo[1, 5-a]pyridines: Easy Access to a New Series of Electrophiles G. Berionni, M. Branca, B. Pégot, J. Marrot, E. Kizilian, R. Goumont, Eur. J. Org. Chem. 2011, 26, 5104-5113. [download] |
Publications 1-10 (Master and PhD work) |
[See my Google Scholar profile] |
Teaching
The link address is: https://directory.unamur.be/staff/gberionn/courses
Open Positions
Projects are currently available in the areas of organoboron chemistry (development of novel Lewis acids, catalysts, receptors), organic reactivity and catalysis (reactivities of frustrated Lewis pairs) and of organometallic chemistry.
If you are interested in pursuing research in any of the areas mentioned above, and would like to discuss the available projects and positions in 2022-2022, please contact Professor Guillaume Berionni by e-mail.
Professor Guillaume Berionni guillaume.berionni@unamur.be
Offre disponible
Postdoctoral position (until May 1st 2023)
Team Pictures
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Group meeting in May 2022 From left to right : Damien Mahaut – Lucie Pedussaut – Ali Ben Saida – Guillaume Berionni – Thu-Hong Doan – Nicolas Niessen – Arnaud Osi – Aurélien Chardon – Bruno Dicarlo – Julien Habrard. |
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Group meeting in July 2021 From left to right : Thu-Hong Doan - Aurélien Chardon - Nicolas Niessen - Mathieu Gama - Arnaud Osi - Damien Mahaut - Jennifer Theissen - Invitée - Dorothée Brandt - Guillaume Berionni - Antoine Willems - Esteban Danloy --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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Group meeting in May 2021 From left to right : Guillaume Berionni - Alain Krief - Thu-Hong Doan - Aurélien Chardon - Jennifer Theissen - Damien Mahaut - Mathieu Gama - Arnaud Osi - Dorothée Brandt - Esteban Danloy - Antoine Willems - Ali Ben Saida --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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Group meeting in July 2020 From left to right : Damien Mahaut - Arnaud Osi - Loic Mineur - Thomas Vanhosmael - Xavier Maes - Thomas Bernard - Guillaume Berionni - Sandrine Dallemagne - Thu-Hong Doan - Nicolas Niessen - Ali Ben Saida - Mathieu Gama --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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Group meeting in September 2019 From left to right : Damien Mahaut - Xavier Antognini Silva – Arnaud Osi - Aurélien Chardon - Thu-Hong Doan - Loïc Mineur - Ali Ben Saida – Prof. Guillaume Berionni – Mathieu Gama – Xavier Maes - (missing Lei Hu) --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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Group meeting in December 2018 (with Prof. Sami Lakhdar) From left to right : Prof. Sami Lakhdar - Catherine Sosson – Prof. Guillaume Berionni - Aurélien Chardon - Damien Mahaut - Ali Ben Saida – Xavier Antognini Silva – Mathieu Gama – Arnaud Osi – Lei Hu --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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| Group meeting in November 2018 (with Prof. Herbert Mayr) From left to right : Catherine Sosson – Ali Ben Saida – Lei Hu – Xavier Antognini Silva – Aurélien Chardon – Prof. Herbert Mayr – Damien Mahaut – Prof. Guillaume Berionni – Arnaud Osi --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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Group meeting in June 2018 (with Prof. Suzanne Blum) From left to right : Damien Mahaut – Lei Hu – Guillaume Berionni – Suzanne Blum – Mathieu Gama – Aurélien Chardon – Ali Ben Saida – Arnaud Osi --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
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First group picture (October 2017) : First group meeting with a special guest : Prof. Alain Krief From left to right : Lei Hu – Guillaume Berionni – Alain Krief – Ali Ben Saida --------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
Events
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Alain Krief symposium - Namur Janvier 2023
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Journées de chimie organique JCO- Paris November 2022
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Mathieu Gama's PhD defence - September 2022
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17th Belgian Organic Synthesis Symposium BOSS - Namur July 2022 ------------------------------------------------------------------------------------------------------------------------------------------------------------------------ |
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Lei HU's PhD defence - November 2020 ------------------------------------------------------------------------------------------------------------------------------------------------------------------------ |
Equipment
Laboratoire de Réactivité et Catalyse Organique (RCO, Professeur Guillaume Berionni)
Laboratories 1&2The RCO team has two laboratories equipped with 10 fume hoods designed for organic and organometallic compounds synthesis. |
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Laboratory 3
In addition to two fume hoods dedicated to synthesis, this laboratory is equipped with a hydrogenation reactor and a low pressure (<50 bar) multi-gas autoclave (H2 ,CO2 ,CH4 , NO2 , N2) allowing to screen and evaluate the ability of new Boron based and organometallic catalysts to activate small gas molecules. |
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In the back of the laboratory is also a high performing glove-box with a built-in refrigerator and a high precision scale allowing to manipulate, stock and weigh air-sensible and moist-sensible catalysts in optimal conditions. |
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Laboratory 4
This last laboratory is divided into two rooms. The first one, the samples preparation room, is equipped with precise measurement glassware, micropipettes and a high precision scale. |
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The second room is equipped with a HPLC-UV-MS (connected to a N2 generator) and a stopped-flow (with a UV-Fluo detector, a PDA, a temperature control system and an automatic titrator). |
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The HPLC-UV-MS(Qda) is a versatile system allowing to take advantage of the chromatography separation with UV detection while benefiting the sensivity and specificity of mass spectrometry. It is an interesting system to do daily analysis on your synthesis to identify different compounds and byproducts. |
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The stopped-flow is a rapid mixing kinetic instrument to study fast reaction in solution in a 1ms to few seconds time window. Two or three reagents are mixed then “stopped” in a UV-florescence observation cell where the light signal variation will be measured through time. The kinetic analysis allows us to determine the reaction speed and to obtain information on complex reactional mechanisms. |
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Common Laboratories
Structural characterization can also be done in the UCO analytical laboratory (UV/Vis spectrometer, fluorimeter, IR spectroscopy …) and with some advanced structural analyzing technologies made available by the NIMS and the PC2 platform (NMR, X-ray crystallography, ICP, HR-MS, microanalysis…) |
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The link address is: https://twitter.com/Dr_Berionni
