laboratoire de Réactivité et Catalyse Organique (RCO)

laboratoire de Réactivité et Catalyse Organique (RCO)

Presentation

Laboratory of Reactivity and Organic Catalysis (RCO, Professor Guillaume Berionni)


Our group's research is mainly focusing on the synthesis and investigation of the reactivities of new Lewis acids derived from triarylboranes and of sterically hindered Lewis bases derived from phosphines and amines, for the rational design of frustrated Lewis pairs. A first strategy, which we have been pursuing for the past years, relies on the uses of new linkers to design FLPs with finely-adjustable geometries and stereo-electronic properties. The catalytic activities of these FLPs (in hydrogenation reactions and small molecules activation) are investigated quantitatively by kinetics investigations, and thermodynamic measurements which allows the subsequent fine-tuning of the FLP catalysts structures.

 

Publications


42

 


Stay tuned : 1 publication submitted

41

pub 41

 

 

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. 2020.

DOI 10.1002/chem.202003319

[download]


40syn

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]

39

Bora

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]

38

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]

 

37

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, 1126811274.

[download]

 

36

 


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]

 

35

 

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]

 

34 organolanthanum

Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles
A. D. Benischke, L. Anthore-Dalion, G. Berionni, P. Knochel, Angew. Chem. Int. Ed. 2017, 51, 16390-16394.
[download]

 

33 allylation 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, 2017, 139, 15324-15327.
[download]
32 borylation

Mechanistic studies of formal thioboration reactions of alkynes
A. Issaian, D. J. Faizi, J. O. Bailey, P. Mayer, G. Berionni*, D. A. Singleton*, S. A. Blum*, J. Org. Chem. 2017, 82, 8165-8178.
[download]

31 lithiathion 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]
30 i_z0304 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]
29 superelectophile 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]
28 chem_toc 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]
27 fluorenyliums 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]
26 zirconocenes 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]
25 frustrated_lewis 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]

24

indolylmethylium

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]
23 alkyl_ate_complexes 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]
22 boron_ate_complexes 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]
21 secondary_alkylithium 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]
20 aromatic_radialenes Aromaticity evaluations of planar [6]radialenes
Guillaume Berionni*, Judy I. Chia Wu, Paul v R. Schleyer, Org. Lett. 2014, 16, 6116-6119
[download]
19 hydride_donors 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]
18 tmpbases 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]
17 electrophilicity 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]
16 diastereoselectives

Diastereoselective Synthesis of Open-Chain Secondary Alkyllithium Compounds and Trapping Reactions with Electrophiles
G Dagousset, K Moriya, R Mose, G Berionni, K Karaghiosoff, P Knochel, Angew. Chem. Int. Ed. 2014, 53, 1425-1429.
[download]

 

15 aromatic_substitution 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]
14 trifluorobates 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]
13 nucleophilicity_scales 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]
12 super_dmap_organocatalysts 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]
11 tetrazolopyridines 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]

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 2020-2021, please contact us by e-mail.

Professor Guillaume Berionni

Team Pictures

 

Equipments

 

 Laboratoire de Réactivité et Catalyse Organique (RCO, Professeur Guillaume Berionni)