Publications Catalyses et hétérocycles

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2022

R. Plais, G. Clavier, J.-Y. Salpin, A. Gaucher, D. Prim
Anion-π Interaction for Molecular Recognition of Anions : Focus on Cooperativity with Hydrogen Bonding
Eur. J. Org. Chem. 2022, e202201281.
DOI : 10.1002/ejoc.202201281


P. De Bonfils, C.Sandoval-Altamirano, X. Moreau, P. Nun, A. Laurent, G. Gunther, V. Coeffard
Synthesis and Photophysical Characterizations of Pyrroloquinolone Photosensitizers for Singlet Oxygen Production
Photochem. Photobiol. 2022, online
DOI : 10.1111/php.13681


R. Plais, G. Gouarin, A. Bournier, O. Zayene, V. Mussard, F. Bourdreux, J. Marrot, A. Brosseau, A. Gaucher, G. Clavier, J.-Y. Salpin, D. Prim
Chloride Binding Modulated by Anion Receptors Bearing Tetrazine and Urea
ChemPhysChem 2022, 23, e202200524.
DOI: 10.1002/cphc.202200524


M. Genet, A. Takfaoui, J. Marrot, C. Greck, X. Moreau.
Organocatalyzed Synthesis of Tetrahydro-alpha-Carboline Derivatives Bearing N,O-Acetals
Eur J. Org. Chem. 2022, 44, e202201154
DOI: 10.1002/ejoc.202201154


W. Ma, E. Montinho-Inacio, B. Iorga, P. Retailleau, X. Moreau, L. Neuville, G. Masson
Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2-Benzothioazolimines
Adv. Synth. Cat. 2022, 364, 1708
DOI: 10.1002/adsc.202200161


A. Abdelli, O. Bejaoui, H. Bougatef, S. Ouni, A. Sila, H. M'rabet, X. Moreau, M. L. Efrit, D. Prim.
Synthesis and evaluation of new phosphonated δ-lactam and glutarimide derivatives as angiotensin converting enzyme inhibitors
J. Heterocyclic. Chem. 2022, online.
DOI:10.1002/jhet.4566.


Y.-C. Yuan, M. Mellah, E. Schulz, O.R.P. David
Making Chiral Salen Complexes Work with Organocatalysts
Chem. Rev. 2022, 122, 8841
DOI:10.1021/acs.chemrev.1c00912


M. Raulin, B. Drouillat, J. Marrot, F. Couty, K. Wright
Diastereoselective ring cleavage of azetidines with cyanogen bromide
Tetrahedron Lett. 2022, 94, 153710
DOI: 10.1016/j.tetlet.2022.153710


A. Sathanikan, G. Ceccone, J. Bañuls-Ciscar, M. Pan, F. Kamal, T. Bsaibess, A. Gaucher, D. Prim, R. Méallet-Renault, P. Colpo, S. Amigoni, F. Guittard, T. Darmanin
A bioinspired approach to fabricate fluorescent nanotubes with strong water adhesion by soft template electropolymerization and post-grafting
J. Colloid Int. Sci. 2022, 606, 236.
DOI : 10.1016/j.jcis.2021.08.013


S. Ouni, A Abdelli, A. Gaucher, Y. Arfaoui, D. Prim, M. L. Efrit
On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study
Chemistry Africa 2022, 5, 1265.
DOI: 10.1007/s42250-022-00452-y


A. Talbi, A. Arfaoui, A. Gaucher, M. L. Efrit, H. M’Rabet, D. Prim
Palladium-Catalyzed Functionalization of α-Methylene Butanolides
Tetrahedron 2022, 122, 132926.
DOI:10.1016/j.tet.2022.132926


F. Guimarães Torres, F. Simões Teodoro, L.V.A. Gurgel, F. Bourdreux, O. Zayene, A. Gaucher, L. F. Gil, D. Prim
Application of natural and chemically modified biomasses to heterogeneous Cu-catalysed conversion of aryl boronic acids to phenols derivatives
Catalysts 2022, 12, 92.
DOI: 10.3390/catal12010092

B. Large, D. Prim
On the Shape and Synthesis of Extended Fluorenones: Recent Advances and Upcoming Challenges
Eur. J Org. Chem. 2022, e202101032 .
DOI: 10.1002/ejoc.202101032

2021

A. Abdelli, S. Azzouni, R. Plais, A. Gaucher, M. L. Efrit, D. Prim
Recent Advances in the Chemistry of 1,2,4- Triazoles: Synthesis, Reactivity and Biological Activities
Tetrahedron Lett. 2021, 86, 153518
DOI: 10.1016/j.tetlet.2021.153518



M. Genet, A. Takfaoui, J. Marrot, C. Greck, X. Moreau
Construction of enantioenriched fused bicyclic piperidines through a multicatalytic sequence merging gold and amine catalysis
Adv. Synth. Catal. 2021, 363, 4516.
DOI : 10.1002/adsc.202100756

W.-Y. Ma, C. Gelis, D. Bouchet, P. Retailleau, X. Moreau, L. Neuville, G. Masson
Chiral Phosphoric Acid Catalyzed Enantioselective Construction of 2,3-Disubstituted Indoline
Org. Lett. 2021, 23, 442.
DOI: 10.1021/acs.orglett.0c03947



F. J. Gonçalves, L. V. A. Gurgel, L. C. Soares, F. S. Teodoro, G. M. D. Ferreira, Y. L Coelho, L. H. M. da Silva, D. Prim, L. F. Gil
Application of pyridine-modified chitosan derivative for simultaneous adsorption of Cu(II) and oxyanions of Cr(VI) from aqueous solution
J. Environ. Manage. 2021, 282, 111939.
DOI: 10.1016/j.jenvman.2021.111939



B. Large, D Prim
Unravelling the C-H arylation of benzo-fused cycloalkanones: combined experimental and computational evidence
Adv. Synth. Catal. 2021, 363, 1685.
DOI:10.1002/adsc.202001349



R. Plais, H. Boufroura, G. Gouarin, A. Gaucher, V. Haldys, A. Brosseau, G. Clavier, J.-Y. Salpin, D. Prim
Design and Property Investigation on a Five-Interaction-based Fluorescent Anion Receptor Clip
RSC Advances 2021, 11, 9476.
DOI: 10.1039/d1ra00630d


 

2020

S. Azzouni, A. Gaucher, D. Prim, M. L. Efrit
Orthogonal arylations of 5-vinyl-1,2,4-triazoles.
Tetrahedron 2020, 76, 130954.
DOI : 10.1016/j.tet.2020.130954

 

A. R Pereira, L. C. Soares, F. S. Teodoro, M. M. Cota Elias, G. M. Dias Ferreira, R. M. Leal Savedra, M. F. Siqueira, C. Martineau-Corcos, L. H. Mendes da Silva, D. Prim, L. V. A. Gurgel
Aminated cellulose as a versatile adsorbent for batch removal of As(V) and Cu(II) from mono- and multicomponent aqueous solutions
J. Colloid Int. Sci. 2020, 576, 158.
DOI : 10.1016/j.jcis.2020.04.129

 

B. Large, R. Plais, A. Gaucher, D. Prim,
Pyridylmethylamines a modular and underrated family of ligands in both metal- and organo-catalysis
Vietnam J. Chem., 2020, 58, 404.
DOI : 10.1002/vjch.202000031.



 

A. Abdelli, H. Gharsa, M. Jmaï, A. Gaucher, M. L. Efrit, H. M’rabet, D. Prim
Versatile approach to densely substituted isoxazolines and pyrazolines: focus on a quaternary carbon center as a constitutive feature
Tetrahedron Lett. 2020, 61, 151958
DOI : 10.1016/j.tetlet.2020.151958.


 

R. Plais, G. Gouarin, A. Gaucher, V. Haldys, A. Brosseau, G. Clavier, J.-Y. Salpin, D. Prim
Intertwined detection and recognition roles of tetrazine in synergistic anion-π and H-bond based anion receptor
ChemPhysChem 2020, 21, 1249.
DOI : 10.1002/cphc.202000289.



 

B. Large, D. Prim
C-H functionalisation strategies in the naphthalene series: site selections and functional diversity
Synthesis, 2020, 2600.
DOI : 10.1055/s-0040-1707855.


 

B. Large, V. Terrasson, D. Prim
Tosylamides in C-H functionalization: more than a simple directing group
Processes 2020, 8(8), 981.
DOI : 10.3390/pr8080981.



 

H. Boufroura, R. Plais, S. Poyer, A. Gaucher, J. Marrot, G. Clavier, F.-X. Legrand, C. Huin, P. Guégan, D. Prim, J.-Y. Salpin
Helically-shaped cation receptor: design, synthesis, characterisation and first application to ion transport
RSC Advances 2020, 10, 31670.
DOI : 10.1039/d0ra05519k.



 

F. Le Guern, V. Mussard, A. Gaucher, M. Rottman, D. Prim
Fluorescein derivatives as fluorescent probes for pH monitoring along recent biological applications
Int. J. Molecular Sciences, 2020, 21(23), 9217.
DOI : 10.3390/ijms21239217.


 

P. De Bonfils, E. Verron, C. Sandoval-Altamirano, P. Jaque, X. Moreau, G. Gunther, P. Nun, V. Coeffard
Unusual oxidative dealkylation strategy toward functionalized phenalenones as singlet oxygen photosensitizers and photophysical studies.
J. Org. Chem. 2020, 85, 10603.
DOI : 10.2021/acs.joc.0c01140.




F. Couty, O. N. Burov, M. E. Kletskii, A. V. Lisovin, K. Wright, B. Drouillat, S. V. Kurbatov
Theoretical investigation of von Braun and von Braun-like reactions
Int. J. Quantum Chem. 2020, 120, 3, e26088
DOI: 10.1002/qua.26088

2019

G. Levitre, C. Audubert, A. Dumoulin, N. Goual, P. Retailleau, X. Moreau, G. Masson
Combining organocatalysis and photoredox catalysis: an asymmetric synthesis of chiral b-amino a-substituted tryptamines
ChemCatChem 2019, 11, 5723 (link)

L. Birbaum, L. Gillard, H. Gérard, H. Oulyadi, G. Vincent, X. Moreau, M. De Paolis, I. Chataigner
Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions
Chem. Eur. J. 2019, 25, 13649 (link)



B. Large, N. Gigant, D. Joseph, G. Clavier, D. Prim.
Site-selective arylation of naphthalenes: a key entry towards extended fluorenones and phenanthridinones
Eur. J. Org. Chem. 2019, 1835 (link)



Y. Filali Baba, Y. Sert, Y. Kandri Rodi, S. Hayani, J.T. Mague, D. Prim, J. Marrot, F. Ouazzani Chahdi, N. Kheira Sebbar, El M. Essassi
Synthesis, crystal structure, spectroscopic characterization, Hirshfeld surface analysis, molecular docking studies and DFT calculations, and antioxidant activity of 2-oxo-1,2-dihydroquinoline-4-carboxylate derivatives
J. Mol. Struct. 2019, 1188, 255 (link)



B. Large, M. Meddeb, J. E. H. Pucheta, A. Gaucher, M. Cordier, C. Gosmini, J. Farjon, A. Auffrant, D. Prim
Deciphering Preferred Geometries of Pyridylmethylamines –Based Complexes: A Robust Strategy Combining NMR, DFT and X-Ray
Inorg. Chim. Acta 2019, 498, 119070 (link)



B. Large, N. Gigant, D. Joseph, G. Clavier, D. Prim
Rhodium‐Catalyzed C–H Activation of Naphthamides for the Synthesis of Substituted 3H‐Benzo[e]isoindolin‐3‐ones
Eur. J. Org. Chem. 2019, 6407 (link)



A.-S. Marques, T. Duhail, J. Marrot, I. Chataigner, V. Coeffard, G. Vincent et X. Moreau
A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4-Dienals by Interrupted iso-Nazarov Reaction
Angew. Chem. Int. Ed. 2019, 58, 9969 (link)



G. R. Chagas, G. M. Cruz, R. Méallet-Renault, A. Gaucher, D. Prim, D. E. Weibel, S. Amigoni, F. Guittard, T. Darmanin
Superhydrophobic and fluorescent properties of fluorinated polypyrene surfaces using various polar linkers prepared via electropolymerization
React. Funct. Polym.  2019, 135, 65 (link)



B.Drouillat, C. Peggion, B. Biondi, K. Wright, F. Couty, M. Crisma, F. Formaggio, C. Toniolo
Heterochiral Ala/(αMe)Aze sequential oligopeptides: Synthesis and conformational study
J. Pep. Sci. 2019, 25, e3165 (link)



P. Quinodoz, K. Wright, B. Drouillat, M. E. Kletskii, O. N. Burov, A. V. Lisovin, F. Couty
α‐Hydroxy‐Tetrazoles as Latent Ethynyl Moieties: A Mechanistic Investigation
Eur. J. Org. Chem. 2019, 342 (link)



K. Wright, B. Drouillat, L. Menguy, J. Marrot, F. Couty
3‑Bromo N‑Alkyl Cyanamides as Versatile Building Blocks
Eur. J. Org. Chem. 2019, 112 (link)

2018

2017

P. Quinodoz, A. Quelhas, K. Wright, B. Drouillat, J. Marrot, F. Couty
Iodocarbamation of N-homopropargyl carbamates : mild and stereoselective entry to functuonalized oxazinan-2-ones
Eur. J. Org. Chem. 2017, 2621 (link)


 

A. Saadaoui, C. Sanglar, R. Medimagh, A. Bonhomme, R. Baudot, S. Chatti, S. Marque, D Prim, M. Said Zina, H. Casabianca
New biosourced chiral molecularly imprinted polymer: Synthesis, characterization and evaluation of the recognition capacity of methyltestosterone.
J. Mol. Recognition 2017, 30, e2594 (link)

M. Giardinetti, J. Marrot, V. Coeffard, X. Moreau, C. Greck
Synthesis and Fluorosolvatochromic Properties of 1,7-Annulated Indoles
New J. Chem. 2017, 41, 7331 (link)

A. Saadaoui, R. Medimagh, S. Marque, D. Prim, S. Chatti, H. Casabianca, M. Said Zina
New biosourced AA and AB monomers from 1,4:3,6-dianhydrohexitols, Isosorbide, Isomannide and Isoidide.
Designed Monomers and Polymers 2017, 20, 221 (link)

O. Colin, H. Boufroura, C. Thomassigny, S. Perato, A. Gaucher, J. Marrot, D. Prim
Modular urea-based catalytic platforms bearing flexible pyridylmethylamine and rigid pyridyl-imidazolidine fragments
Eur. J. Org. Chem. 2017, 746 (link)


 

S. Perato, B. Large, Q. Lu, A. Gaucher, D. Prim
Pyridylmethylamine-Pd catalytic systems, a selective alternative in C-H arylation of indole
ChemCatChem 2017, 9, 389 (link)

H. Boufroura, B. Large, T. Bsaibess, S. Perato, V. Terrasson, A. Gaucher, D. Prim
Aziridine- and azetidine-Pd catalytic combinations. Synthesis and evaluation of the ligand ring size impact on Suzuki-Miyaura reaction issues.
Catalysts 2017, 7, 27 (link)

H. Boufroura, A. Abdelli, T. Bsaibess, F. Bourdreux, A. Gaucher,G. Clavier, M. L. Efrit, H. M’Rabet, D. Prim
Easy access to 1,2-azaphospholidines through novel one pot nucelophilic addition -  aza-Michael addition sequence. Extension to the preparation of azaphosphacane and azaphosphanane analogues.
RSC Advances 2017, 7, 18211 (link)

K. Wright, B. Drouillat, L. Menguy, J. Marrot, F. Couty
The Von Braun reaction applied to azetidines
Eur. J. Org. Chem. 2017, 7195  (link)

A. Talbi, A. Arfaoui, T. Bsaibess, M. L. Efrit, A. Gaucher, D. Prim, H. M’Rabet
Selective synthesis of mono- and bis-butenolides -aminomethyl adducts
Org. Biomol. Chem. 2017, 15, 3298 (link)


 

A. Talbi; T. bsaibess; M. L. Efrit; H. M’Rabet; A. Gaucher, D. Prim
Straightforward and regioselective access to α-benzyl unsaturated butyrolactones
Eur. J. Org. Chem. 2017, 5246 (link)

S. Bezzenine-Lafollée, R. Gil, D. Prim, J. Hannedouche
First-row late transition metals for catalytic alkene hydrofunctionalisation: Recent advances in C-N, C-O and C-P bond formation
Molecules 2017, 22, 1901 (link)

A. Talbi, A. Gaucher, F. Bourdreux, J. Marrot, M. L. Efrit, H. M’Rabet, D. Prim
From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
Molecules 2017, 22, 2171 (link)

L. Pantaine, A. Laverny, X. Moreau, V. Coeffard, C. Greck
Stereoselective multibond-forming process towards functionalized sulfamide-containing polycycles
Synthesis 2017, 49, 532 (link)

 

2016

 

S. Feuillastre, M. Pauton, L. Gao, A. Desmarchelier, A. Riives, D. Prim, D. Tondelier, B. Geffroy, G. Muller, G. Clavier, G. Pieters
Design and synthesis of new circularly polarized thermally activated delayed fluorescence emitters.
J. Am. Chem. Soc. 2016, 138, 3990 (link)

B. Drouillat, I. V. Dorogan, M. Kletskii, O. N. Burov, F. Couty
Competitive Ring Expansion of Azetidines into Pyrrolidines and/or Azepanes
J. Org. Chem. 2016, 81, 6677 (link)

A.-S. Marques, V. Coeffard, I. Chataigner, G. Vincent, X. Moreau
Iron-mediated domino interrupted iso-Nazarov/dearomative (3+2)-cycloaddition of electrophilic indoles
Org. Lett. 2016, 18, 5296 (link)

P. Quinodoz, B. Drouillat, K. Wright, J. Marrot, F. Couty
N‑Arylazetidines: Preparation through Anionic Ring Closure
J. Org. Chem. 2016, 81, 2899 (link)


 

A. Abdelli, F. Bourdreux, A. Gaucher, M. L. Efrit, H. M’rabet, D. Prim
Ring-closing metathesis on deactivated allyl-phosphonates and -phosphoramidates: access to dihydrophosphinine oxides bearing an ester group.
Tetrahedron Lett. 2016, 57, 379 (link)


 

M. Giardinetti, J. Marrot, X. Moreau, V. Coeffard, C. Greck
Asymmetric Synthesis of Fused Polycyclic Indazoles through Aminocatalyzed Aza-Michael Addition/Intramolecular Cyclization
J. Org. Chem. 2016, 81, 6855 (link)


 

J. E. Herbert Pucheta, J.-M. Gillet, D. Prim, J. Farjon
Deciphering the conformational choreography of Zn-coordination complexes with the help of standard and novel proton NMR techniques combined with DFT methods.
ChemPhysChem 2016, 17, 1034 (link)

G. Ramos Chagas, X. Xie, T. Darmanin, K. Steenkeste, A. Gaucher, D. Prim, R. Meallet-Renault, S. Amigoni, G. Godeau, F. Guittard
Electrodeposition of Polypyrenes with Tunable Hydrophobicity, Water Adhesion and Fluorescence Properties.
J. Phys. Chem. C. 2016, 120, 7077 (link)


 

P. Quinodoz, K. Wright, B. Drouillat, O. David, J. Marrot, F. Couty
Synthesis of homopargylamines from 2-cyanoazetidines
Chem. Commun. 2016, 52, 10072 (link)

A. Aillerie, V. Rodriguez-Ruiz, R. Carlino, F. Bourdreux, R. Guillot, S. Bezzenine-Lafollée, R. Gil, D. Prim, J. Hannedouche
Asymmetric Assisted Tandem Catalysis: Hydroamination followed by Asymmetric Friedel-Crafts reaction from a single chiral N, N, N’, N’-tetradentate pyridylmethylamine-based ligand.
ChemCatChem. 2016, 8, 2455 (link)

L. Pantaine, F. Richard, J. Marrot, X. Moreau, V. Coeffard, C. Greck
Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen-Like Rearrangement
Adv. Synth. Catal. 2016, 358, 2012 (link)

A.-S. Marques, M. Giardinetti, J. Marrot, V. Coeffard, X. Moreau, C. Greck
Construction of enantioenriched polysubstituted hexahydropyridazines via a sequential multicatalytic process merging palladium catalysis and aminocatalysis
Org. Biomol. Chem. 2016, 14, 2828 (link)


 

K. J. Broadley, M. G. P. Buffat, E. Burnell, R. H. Davies, X. Moreau, S. Snee, E. J. Thomas
Stereoselective synthesis of oxazolidinonyl-fused piperidines of interest as muscarinic (M-1) receptor agonists: a novel M-1 allosteric modulator
Org. Biomol. Chem. 2016, 14, 2057 (link)



Loïc Pantaine, Xavier Moreau, Vincent Coeffard, and Christine Greck
The impact of asymmetric organocatalysis in dearomatization and aromatization of carbocycles: increasing molecular complexity and diversity
Tet. Lett. 2016, 57, 2567 (link)