Polycyclisations Catalytiques
Over the past 5 years, our group has remained focused on the development of original homogeneous catalytic methods towards the synthesis of cyclic compounds.One aspect of our work aims at circumventing the limitations of late transition metal catalysis by devising new activation protocols that allow to control the decomposition of the complex and therefore significantly diminish its loading. The second aspect is to replace noble metals by more abundant elements from the first row transition metal series, or by main group metals. All these projects have been supported by computational studies to rationalize the reaction mechanisms. Computational chemistry, especially DFT calculations, still occupies a prominent position in the group and constitutes on its own the third aspect of our investigations.
We have exploited the exceptional σ-Lewis acidity of Ca(II) complex, sometimes exacerbated by the use of hexafluoroisopropanol as solvent (HFIP), to activate electron-poor C=C bonds in hydroamination reactions, or to activate Csp3-O bonds for the synthesis of carbocycles or oxygen- or nitrogen-containing heterocycles. In particular, the low-tech air-stable calcium pre-catalyst Ca(NTf2)2 showed an exceptional versatility in reactions leading to furans, pyrroles or pyrrolidines.
The borrowing hydrogen strategy has been applied to the ethylation of imines, using an air-stable iron complex as precatalyst. This approach has opened new perspectives in this area, as it allowed the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as C2-building block. A variety of imines bearing electron-rich aromatic or alkyl groups at the nitrogen atom could be efficiently reductively alkylated, without requiring the use of molecular hydrogen.
We have developed new families of cationic Ga(I), Ga(III), In(I) and In(III) catalysts able to imitate the behavior of noble transition metal complexes in π-acid catalysis or transfer hydrogenation. These species exhibit either NHC or fluorobenzene ligands. They behave as soft Lewis acids able to trigger the formation of highly delocalized non-classical carbocations from alkynes and alkenes. They are especially useful in skeletal reorganization reactions leading to polycyclic compounds after C-C or C-H bond formation.
In order to improve the overall efficiency of gold-catalyzed transformations, we have discovered that Cu(I) and Cu(II) salts could activate LAuCl precatalysts, while lowering their decay into inactive nanoparticles. This decomposition phenomenon is typically observed with Ag(I) activators, which are commonly used to generate the active cationic gold complex. On the other hand, the Au/Cu catalytic system proved versatile and allowed to carry out a variety of reactions with very low loadings of the gold precatalyst and without requiring tedious ligand design. Indeed, simple phosphines could be used successfully on gram-scale reactions.
In addition to providing a mechanistic insight into the aforementioned and other in-house projects, DFT computations have been carried out on various collaborative projects on Au-, Rh-, Fe-, Pd-catalyzed reactions and other catalytic processes leading to polycyclic compounds. Among recent achievements, we have deciphered the intriguing Pd-catalyzed carbocyclization leading to polycyclic cyclooctatetraenes in collaboration with J. Suffert and G. Blond from Unistra.
Recent publications:
Atroposelective Synthesis of Tetrahydropyrrolo[3,2-c]azepine Derivatives Through Gold(I)-Catalyzed Hydroarylation. Q. Gaignard-Gaillard, X. Han, A. Alix, C. Bour, R. Guillot, V. Gandon, A. Voituriez, Advanced Synthesis & Catalysis, 2022, n/a
Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles. N. Sabat, W. Zhou, V. Gandon, X. Guinchard, G. Vincent, Angewandte Chemie, International Edition, 2022, 61, e202204400
Expedient Access to Polyaromatic Biaryls by Unconventional Ag-Catalyzed Cycloaromatization of Alkynylthiophenes and Au-Catalyzed Double C-H Activation. R. K. Saunthwal, K. M. Saini, N. Grimblat, A. K. Danodia, S. Kumar, V. Gandon, A. K. Verma, Organic Letters, 2022, 24, 5018-5022
Polyarylquinone Synthesis by Relayed Dehydrogenative [2+2+2] Cycloaddition. S. Hore, A. Singh, S. De, N. Singh, V. Gandon, R. P. Singh, ACS Catalysis, 2022, 12, 6227-6237
A cyclic divalent N(I) species isoelectronic to carbodiphosphoranes. J. Tian, M. Cordier, C. Bour, A. Auffrant, V. Gandon, Chemical Communications (Cambridge, United Kingdom), 2022, 58, 5741-5744
Palladium-Catalyzed Silylcyanation of Ynamides: Regio- and Stereoselective Access to Tetrasubstituted 3-Silyl-2-Aminoacrylonitriles. P. Hansjacob, F. R. Leroux, V. Gandon, M. Donnard, Angewandte Chemie, International Edition, 2022, 61, e202200204
Palladium-Catalyzed Regioselective Arylalkenylation of Ynamides. R. Vanjari, S. Dutta, S. Yang, V. Gandon, A. K. Sahoo, Organic Letters, 2022, 24, 1524-1529
Transition structures for the oxy-ene reaction. S. Yang, S. Miaskiewicz, C. Bour, A. Alix, V. Gandon, Chemical Communications (Cambridge, United Kingdom), 2022, 58, 4751-4754
Synthesis of chiral polycyclic N-heterocycles via gold(I)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition. X. Han, Q. Gaignard-Gaillard, P. Retailleau, V. Gandon, A. Voituriez, Chemical Communications (Cambridge, United Kingdom), 2022, 58, 3043-3046
Cationic-palladium catalyzed regio- and stereoselective syn-1,2-dicarbofunctionalization of unsymmetrical internal alkynes. S. Dutta, S. Shandilya, S. Yang, M. P. Gogoi, V. Gandon, A. K. Sahoo, Nature Communications, 2022, 13, 1360
Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles. N. Sabat, W. Zhou, V. Gandon, X. Guinchard, G. Vincent, Angew. Chem. Int. Ed., 2022, 61, e202204400
Leveraging the Domino Skeletal Expansion of Thia-/Selenazolidinones via Nitrogen-Atom Transfer in HFIP: Room Temperature Access to Six-Membered S/Se,N-Heterocycles. V. Jaiswal, M. Godara, D. Das, V. Gandon, J. Saha, J. Org. Chem., 2022, 87, 613-627
Potassium Carbonate to Unlock a GaCl3-Catalyzed C–H Propargylation of Arenes. M. Vayer, S. Rodrigues, S. Miaskiewicz, D. Gatineau, Y. Gimbert, V. Gandon, C. Bour, ACS Catal., 2022, 12, 305-315
Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Pd(II)-MPAA Catalyzed C-H Arylation and Olefination. K. Mukherjee, N. Grimblat, S. Sau, K. Ghosh, M. Shankar, V. Gandon, A. K. Sahoo, Chem. Sci., 2021, 12, 14863–14870
Synthesis of Axially Chiral Biaryl Thioglycosides through Thiosugar-Directed Pd-Catalyzed Asymmetric C–H Activation. N. Fatthalla, N. Grimblat, E. Brachet, M. Alami, F. Le Bideau, V. Gandon, S. Messaoudi, Chem. Commun., 2021, 57, 10355-10358
Hexafluoroisopropanol-Promoted Haloamidation and Halolactonization of Unactivated Alkenes. C. Qi, G. Force, V. Gandon, D. Lebœuf, Angewandte Chemie, International Edition, 2021, 60, 946-953
Modular Synthesis of 9,10-Dihydroacridines through an ortho-C Alkenylation/Hydroarylation Sequence between Anilines and Aryl Alkynes in Hexafluoroisopropanol. S. Wang, G. Force, J.-F. Carpentier, Y. Sarazin, C. Bour, V. Gandon, D. Lebœuf, Organic Letters, 2021, 23, 2565-2570
Zirconium-Catalyzed Hydroalumination of C=O Bonds: Site-Selective De-O-acetylation of Peracetylated Compounds and Mechanistic Insights. T. Courant, M. Gavel, R. M. Q. Renard, V. Gandon, A. Y. P. Joosten, T. Lecourt, Journal of Organic Chemistry, 2021, 86, 9280-9288
DFT Analysis into the Calcium(II)-Catalyzed Coupling of Alcohols With Vinylboronic Acids: Cooperativity of Two Different Lewis Acids and Counterion Effects. S. Yang, C. Bour, D. Lebœuf, V. Gandon, Journal of Organic Chemistry, 2021, 86, 9134-9144
Yb(III)-catalysed syn-thioallylation of ynamides. M. P. Gogoi, R. Vanjari, B. Prabagar, S. Yang, S. Dutta, R. K. Mallick, V. Gandon, A. K. Sahoo, Chemical Communications (Cambridge, United Kingdom), 2021, 57, 7521-7524
Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition. T. Varlet, M. Matisic, E. Van Elslande, L. Neuville, V. Gandon, G. Masson, Journal of the American Chemical Society, 2021, 143, 11611-11619
Reaction of Phosphines with 1-Azido-(2-halogenomethyl)benzene Giving Aminophosphonium-Substituted Indazoles. T. Tannoux, N. Casaretto, S. Bourcier, V. Gandon, A. Auffrant, Journal of Organic Chemistry, 2021, 86, 3017-3023
Concerted vs Nonconcerted Metalation-Deprotonation in Orthogonal Direct C-H Arylation of Heterocycles with Halides: A Computational Study. V. Gandon, C. Hoarau, Journal of Organic Chemistry, 2021, 86, 1769-1778
Diastereoselective Pd-Catalyzed Anomeric C(sp3)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides. J. Ghouilem, C. Tran, N. Grimblat, P. Retailleau, M. Alami, V. Gandon, S. Messaoudi, ACS Catalysis, 2021, 11, 1818-1826
Harnessing sulfur and nitrogen in the cobalt(III)-catalyzed unsymmetrical double annulation of thioamides: probing the origin of chemo- and regio-selectivity. M. Shankar, A. Saha, S. Sau, A. Ghosh, V. Gandon, A. K. Sahoo, Chemical Science, 2021, 12, 6393-6405
Alkynophilicity of Group 13 MX3 Salts: A Theoretical Study. S. Yang, A. Alix, C. Bour, V. Gandon, Inorganic Chemistry, 2021, 60, 5507-5522
Gold-Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration. P. Milcendeau, V. Gandon, X. Guinchard, Advanced Synthesis & Catalysis, 2021, 363, 2893-2902
Sulfoxide-Controlled Stereoselective Aza-Piancatelli Reaction. L. Marin, S. Jerhaoui, E. Kolodziej, R. Guillot, V. Gandon, F. Colobert, E. Schulz, J. Wencel-Delord, D. Leboeuf, Advanced Synthesis & Catalysis, 2021, 363, 4277-4282
Alkylidene Meldrum’s Acids as Novel Platforms for the Vinylogous Synthesis of Dihydropyranones. G. Vo-Thanh, S. Wittmann, T. Martzel, C.-T. Pham Truong, M. Toffano, S. Oudeyer, R. Guillot, C. Bournaud, V. Gandon, J.-F. Brière, Angewandte Chemie International Edition, 2021, 60, 11110-11114
Cobalt-Catalyzed C(sp2)-CN Bond Activation: Cross-Electrophile Coupling for Biaryl Formation and Mechanistic Insight. C. Dorval, M. Tricoire, J.-M. Begouin, V. Gandon, C. Gosmini, ACS Catalysis, 2020, 10, 12819-12827
Sequential One-Pot Synthesis of 3-Arylbenzofurans from N-Tosylhydrazones and Bromophenol Derivatives. D. Lamaa, C. Hauguel, H.-P. Lin, E. Messe, V. Gandon, M. Alami, A. Hamze, Journal of Organic Chemistry, 2020, 85, 13664-13673
Exploring the Limits of π-Acid Catalysis Using Strongly Electrophilic Main Group Metal Complexes: The Case of Zinc and Aluminium. J. Tian, Y. Chen, M. Vayer, A. Djurovic, R. Guillot, R. Guermazi, S. Dagorne, C. Bour, V. Gandon, Chemistry – A European Journal, 2020, 26, 12831 - 12838
On the Superior Activity of In(I) versus In(III) Cations Toward ortho-C-Alkylation of Anilines and Intramolecular Hydroamination of Alkenes. Z. Li, S. Yang, G. Thiery, V. Gandon, C. Bour, J. Org. Chem., 2020
Exploiting Hexafluoroisopropanol (HFIP) in Lewis and Bronsted Acid-Catalyzed Reactions. V. Pozhydaiev, M. Power, V. Gandon, J. Moran, D. Lebœuf, Chemical Communications (Cambridge, United Kingdom), 2020, 56, 11548-11564
Solvent Effect in Gold(I)-Catalyzed Domino Reaction: Access to Furopyrans. P. Wagner, N. Ghosh, V. Gandon, G. Blond, Organic Letters, 2020, 22, 7333-7337
Lewis Acid/Hexafluoroisopropanol: A Promoter System for Selective ortho-C-Alkylation of Anilines with Deactivated Styrene Derivatives and Unactivated Alkenes. S. Wang, G. Force, R. Guillot, J.-F. Carpentier, Y. Sarazin, C. Bour, V. Gandon, D. Lebœuf, ACS Catalysis, 2020, 10, 10794-10802
Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D. L. Marin, G. Force, V. Gandon, E. Schulz, D. Lebœuf, European Journal of Organic Chemistry, 2020, 2020, 5323-5328
Enantioselective gold(I)-catalyzed cyclization/intermolecular nucleophilic additions of 1,5-enyne derivatives. X. Han, P. Retailleau, V. Gandon, A. Voituriez, Chemical Communications (Cambridge, United Kingdom), 2020, 56, 9457-9460
Double annulation of ortho- and peri-C-H bonds of fused (hetero)arenes to unusual oxepino-pyridines. M. Shankar, R. K. Rit, S. Sau, K. Mukherjee, V. Gandon, A. K. Sahoo, Chemical Science, 2020, 11, 10770-10777
Regio- and diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides. J. Ghouilem, R. Franco, P. Retailleau, M. Alami, V. Gandon, S. Messaoudi, Chemical Communications (Cambridge, United Kingdom), 2020, 56, 7175-7178
Keteniminium-Driven Umpolung Difunctionalization of Ynamides. S. Dutta, S. Yang, R. Vanjari, R. K. Mallick, V. Gandon, A. K. Sahoo, Angewandte Chemie, International Edition, 2020, 59, 10785-10790
Base-Assisted Intramolecular C-N Coupling Reaction from NH2-Bound Cyclopalladated L-Phenylalanine to Indoline-2-carboxylic Acid. A. Jacquin-Labarre, S. Coufourier, R. Tamion, A. Le Foll, V. Levacher, C. Afonso, V. Gandon, G. Journot, J.-F. Briere, C. Hoarau, Organometallics, 2020, 39, 767-773
Tridentate NNN Ligand Associating Amidoquinoline and Iminophosphorane: Synthesis and Coordination to Pd and Ni Centers. L. Mazaud, M. Tricoire, S. Bourcier, M. Cordier, V. Gandon, A. Auffrant, Organometallics, 2020, 39, 719-728
Superelectrophilic Gallium(III) Homodimers in Gallium Chloride-Mediated Methylation of Benzene: A Theoretical Study. S. Yang, C. Bour, V. Gandon, ACS Catalysis, 2020, 10, 3027-3033
An unconventional sulfur-to-selenium-to-carbon radical transfer: chemo-and regioselective cyclization of yne-ynamides. S. Dutta, B. Prabagar, R. Vanjari, V. Gandon, A. K. Sahoo, Green Chemistry, 2020, 22, 1113-1118
Enantioselective Synthesis of Complex Fused Heterocycles through Chiral Phosphoric Acid Catalyzed Intramolecular Inverse-Electron-Demand Aza-Diels-Alder Reactions. L. Jarrige, V. Gandon, G. Masson, Chemistry - A European Journal, 2020, 26, 1406-1413
Alkaline-earth complexes with macrocyclic-functionalised bis(phenolate)s and bis(fluoroalkoxide)s. J. Hammoud, F. Abou-Khalil, T. Roisnel, V. Dorcet, C. Bour, V. Gandon, D. Leboeuf, J.-F. Carpentier, Y. Sarazin, Dalton Trans., 2020
Exploring the Versatility of 7-Alkynylcycloheptatriene Scaffolds Under π-Acid Catalysis. M. Vayer, C. Bour, V. Gandon, European Journal of Organic Chemistry, 2020, n/a
Bimolecular vinylation of arenes by vinyl cations. Z. Li, V. Gandon, C. Bour, Chem. Commun., 2020
Formal [8+3]-Annulation between Azaoxyallyl Cations and Tropones. G. Force, A. Pérot, R. Guillot, V. Gandon, D. Leboeuf, Synthesis, 2020, 52, 553-564
Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli Cyclization/Michael Addition Sequence. S. Wang, R. Guillot, J.-F. Carpentier, Y. Sarazin, C. Bour, V. Gandon, D. Lebœuf, Angewandte Chemie, 2020, 132, 1150-1154
Enantioselective Total Synthesis of Cymoside through a Bioinspired Oxidative Cyclization of a Strictosidine Derivative. Y. Dou, C. Kouklovsky, V. Gandon, G. Vincent, Angew. Chem. Int. Ed., 2020, 59, 1527-1531
Asymmetric Cu(I)-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si-H Bonds. V. Carreras, C. Besnard, V. Gandon, T. Ollevier, Organic Letters, 2019, 21, 9094-9098
Toward a Greener Barluenga-Valdes Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System. D. Lamaa, E. Messe, V. Gandon, M. Alami, A. Hamze, Organic Letters, 2019, 21, 8708-8712
Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli Cyclization/Michael Addition Sequence. S. Wang, R. Guillot, J.-F. Carpentier, Y. Sarazin, C. Bour, V. Gandon, D. Leboeuf, Angewandte Chemie International Edition, 2019, 59, 1134-1138
Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol. G. Zhao, C. Roudaut, V. Gandon, M. Alami, O. Provot, Green Chemistry, 2019, 21, 4204-4210
Gold(I)-Catalyzed Synthesis of Furopyrans: Insight into Hetero-Diels-Alder Reactions. R. Pertschi, P. Wagner, N. Ghosh, V. Gandon, G. Blond, Organic Letters, 2019, 21, 6084-6088
Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels-Alder Reactions. V. Le Fouler, Y. Chen, V. Gandon, V. Bizet, C. Salome, T. Fessard, F. Liu, K. N. Houk, N. Blanchard, Journal of the American Chemical Society, 2019, 141, 15901-15909
Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol. C. Qi, S. Yang, V. Gandon, D. Lebœuf, Organic Letters, 2019, 21, 7405-7409
Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation. A. Djurovic, M. Vayer, Z. Li, R. Guillot, J.-P. Baltaze, V. Gandon, C. Bour, Organic Letters, 2019, 21, 8132-8137
Stereoselective Access to (E)-1,3-Enynes through Pd/Cu-Catalyzed Alkyne Hydrocarbation of Allenes. L. Jeanne-Julien, G. Masson, R. Kouoi, A. Regazzetti, G. Genta-Jouve, V. Gandon, E. Roulland, Organic Letters, 2019, 21, 3136-3141
Gold-Catalyzed Regioselective Tetradehydro-Diels-Alder Reaction of Yne-Ynamides: Access to 2,3-Dihydrobenzo[f]indoles. B. Prabagar, S. Dutta, V. Gandon, A. K. Sahoo, Asian Journal of Organic Chemistry, 2019, 8, 1128-1132
Photooxygenation of 2-propargylfurans: a path to structurally diverse nitrogen-containing 5-membered rings. L. Marin, G. Force, R. Guillot, V. Gandon, E. Schulz, D. Lebœuf, Chem. Commun., 2019, 55, 5443-5446
Alkyne Versus Ynamide Reactivity: RegioselectiveRadical Cyclization of Yne-Ynamides. V. Gandon, S. Dutta, R. K. Mallick, R. Prasad, A. K. Sahoo, Angew. Chem. Int. Ed., 2019, 58, 2289 –2294
Umpolung Reactivity of Ynamides: An Unconventional [1,3]-Sulfonyl and [1,5]-Sulfinyl Migration Cascade. V. Gandon, B. Prabagar, R. K. Mallick, R. Prasad, A. K. Sahoo, Angew. Chem. Int. Ed., 2019, 58, 2365 –2370
Bimetallic gold(I) complexes of photoswitchable phosphines: synthesis and uses in cooperative catalysis. T. Arif, C. Cazorla, N. Bogliotti, N. Saleh, F. Blanchard, V. Gandon, R. Metivier, J. Xie, A. Voituriez, A. Marinetti, Catalysis Science & Technology, 2018, 8, 710-715
Selectivity in the Intermolecular Diels-Alder Reaction of Conjugated Trienes: Experimental and Theoretical Approaches. C. Remeur, S. Desrat, V. Gandon, F. Roussi, European Journal of Organic Chemistry, 2018, 2018, 5869-5877
Iodine-Catalyzed Iso-Nazarov Cyclization of Conjugated Dienals for the Synthesis of 2-Cyclopentenones. L. A. Marsili, J. L. Pergomet, V. Gandon, M. J. Riveira, Organic Letters, 2018, 20, 7298-7303
Empirical Estimation of the Molecular Weight of Gold Complexes in Solution by Pulsed-Field Gradient NMR. G. Hamdoun, C. Bour, V. Gandon, J.-N. Dumez, Organometallics, 2018, 37, 4692-4698
Gold-Catalyzed syn-1,2-Difunctionalization of Ynamides via Nitrile Activation. R. Vanjari, S. Dutta, M. P. Gogoi, V. Gandon, A. K. Sahoo, Organic Letters, 2018, 20, 8077-8081
Synthesis of Cyclopenta[b]piperazinones via an Azaoxyallyl Cation. B. Baldé, G. Force, L. Marin, R. Guillot, E. Schulz, V. Gandon, D. Lebœuf, Org. Lett., 2018, 20, 7405-7409
Gallium-Catalyzed Scriabine Reaction. M. Pareek, C. Bour, V. Gandon, Org. Lett., 2018, 20, 6957-6960
Calcium(II)-Catalyzed Intermolecular Hydroarylation of Deactivated Styrenes in Hexafluoroisopropanol. C. Qi, V. Gandon, D. Lebœuf, Angewandte Chemie International Edition, 2018, 57, 14245-14249
Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp3)-H Arylation of Glycosides. N. Probst, G. Grelier, S. Dahaoui, M. Alami, V. Gandon, S. Messaoudi, ACS Catalysis, 2018, 8, 7781-7786
Spatially encoded diffusion-ordered NMR spectroscopy of reaction mixtures in organic solvents. G. Hamdoun, L. Guduff, C. Van Heijenoort, C. Bour, V. Gandon, J.-N. Dumez, Analyst, 2018, 143, 3458-3464
Synthesis of 3-Substituted 3-Bromo-1-phenylallenes from Alkynylcycloheptatrienes. M. Vayer, R. Guillot, C. Bour, V. Gandon, J. Org. Chem., 2018, 83, 11309–11317
Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol Alcohol. C. Qi, F. Hasenmaile, V. Gandon, D. Lebœuf, ACS Catalysis, 2018, 8, 1734-1739
Intermolecular rhodium(II)-catalyzed allylic C(sp3)-H amination of cyclic enamides. R. Rey-Rodriguez, G. Jestin, V. Gandon, G. Grelier, P. Retailleau, B. Darses, P. Dauban, I. Gillaizeau, Advanced Synthesis & Catalysis, 2018, 360, 513-518
Reactions Involving Tryptamines and δ-Allenyl Aldehydes: Competition between Pictet-Spengler Reaction and Cyclization to 1-Aminotetralins. V. Gobe, V. Gandon, X. Guinchard, Advanced Synthesis & Catalysis, 2018, 360, 1280-1288
Iron-Catalyzed Reductive Ethylation of Imines with Ethanol. M. Vayer, S. P. Morcillo, J. Dupont, V. Gandon, C. Bour, Angewandte Chemie, International Edition, 2018, 57, 3228-3232
Dissecting the Gold(I)-Catalyzed Carboaminations of N-Allyl Tetrahydro-β-carbolines to Allenes. V. Gobe, M. Dousset, P. Retailleau, V. Gandon, X. Guinchard, Journal of Organic Chemistry, 2018, 83, 898-912
A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(ii)/copper(ii) catalytic sequence. L. Marin, R. Guillot, V. Gandon, E. Schulz, D. Lebœuf, Org. Chem. Front., 2018, 5, 640-647
Catalytic Use of Low-Valent Cationic Gallium(I) Complexes as π-Acids. Z. Li, G. Thiery, M. R. Lichtenthaler, R. Guillot, I. Krossing, V. Gandon, C. Bour, Advanced Synthesis & Catalysis, 2018, Volume360, Issue3, 544-549
Triflic acid as an efficient Brønsted acid promoter for the Umpolung of N-Ac indoles in hydroarylation reactions. R. K. Nandi, A. Perez-Luna, D. Gori, R. Beaud, R. Guillot, C. Kouklovsky, V. Gandon, G. Vincent, Adv. Synth. Catal., 2018, 360, 161–172
Functionalization of Mo132 Keplerate Nanocapsules by Cyclic Carboxylates: L-proline vs Cyclopentanecarboxylate. M. Awada, S. Floquet, M. Haouas, N. Watfa, J. Marrot, C. Roch-Marchal, V. Coeffard, C. Greck, C. Bour, V. Gandon, F. Taulelle, E. Cadot, Current Inorganic Chemistry, 2017, 7, 39-47
Intramolecular Inverse Electron-Demand [4 + 2] Cycloadditions of Ynamides with Pyrimidines: Scope and Density Functional Theory Insights. G. Duret, R. Quinlan, B. Yin, R. E. Martin, P. Bisseret, M. Neuburger, V. Gandon, N. Blanchard, Journal of Organic Chemistry, 2017, 82, 1726-1742
Carbon-Carbon and Carbon-Heteroatom Bond-Forming Transformations Catalyzed by Calcium(II) Triflimide. D. Lebœuf, V. Gandon, Synthesis, 2017, 49, 1500-1508
Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions. A. Joosten, M. Boultadakis-Arapinis, V. Gandon, L. Micouin, T. Lecourt, Journal of Organic Chemistry, 2017, 82, 3291-3297
Calcium(II)-Catalyzed Alkenylation of N-Acyliminiums and Related Ions with Vinylboronic Acids. C. Qi, V. Gandon, D. Lebœuf, Advanced Synthesis & Catalysis, 2017, 359, 2671-2675
Enantioselective gold(I)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes. Z. Wu, D. Lebœuf, P. Retailleau, V. Gandon, A. Marinetti, A. Voituriez, Chemical Communications (Cambridge, United Kingdom), 2017, 53, 7026-7029
Intramolecular Pd-Catalyzed Anomeric C(sp3)-H Activation of Glycosyl Carboxamides. N. Probst, G. Grelier, N. Ghermani, V. Gandon, M. Alami, S. Messaoudi, Organic Letters, 2017, 19, 5038-5041
Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines. V. Magne, A. Marinetti, V. Gandon, A. Voituriez, X. Guinchard, Advanced Synthesis & Catalysis, 2017, 359, 4036-4042
Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives. S. Lauzon, H. Keipour, V. Gandon, T. Ollevier, Organic Letters, 2017, 19, 6324-6327
One-Pot Assembly of Highly Functionalized Cyclopenta[b]pyrroles via a Calcium(II)- and Copper(II)-Catalyzed Reaction Sequence. L. Marin, V. Gandon, E. Schulz, D. Lebœuf, Advanced Synthesis & Catalysis, 2017, 359, 1157-1163
Revealing the Activity of pi-Acid Catalysts Using a 7-Alkynyl Cycloheptatriene. V. Gandon, M. Vayer, R. Guillot, C. Bour, Chemistry – A European Journal, 2017, Volume 23, Issue 56, 13901–13905
Revealing the Electrophilicity of N-Ac Indoles with FeCl3: a mechanistic study. R. Beaud, R. K. Nandi, A. Perez-Luna, R. Guillot, D. Gori, C. Kouklovsky, N. E. Ghermani, V. Gandon, G. Vincent, Chem. Commun., 2017, 53, 5834 - 5837
Catalytic Activity of Gold(I) Complexes with Hemilabile P,N Ligands. B. Michelet, D. Lebœuf, C. Bour, K. Škoch, F. Horký, P. Štěpnička, V. Gandon, ChemPlusChem, 2017, 82, 442-448
Synthesis and Characterizations of Keplerate Nanocapsules Incorporating L- and D-Tartrate Ligands. M. Awada, S. Floquet, J. Marrot, M. Haouas, S. P. Morcillo, C. Bour, V. Gandon, V. Coeffard, C. Greck, E. Cadot, Journal of Cluster Science, 2017, 1-14
Synthesis, biological evaluation and molecular modeling studies on novel quinonoid inhibitors of CDC25 phosphatases. E. Evain-Bana, L. Schiavo, C. Bour, D. A. Lanfranchi, S. Berardozzi, F. Ghirga, D. Bagrel, B. Botta, G. Hanquet, M. Mori, Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, 32, 113
Acid-catalysed intramolecular addition of [small beta]-ketoesters to 1,3-dienes. M. Vayer, W. Fang, R. Guillot, S. Bezzenine-Lafollee, C. Bour, V. Gandon, Org. Biomol. Chem., 2017, 15, 584-588
Calcium‐Catalyzed Synthesis of Polysubstituted 2‐Alkenylfurans from β‐Keto Esters Tethered to Propargyl Alcohols. S. P. Morcillo, D. Lebœuf, C. Bour, V. Gandon, Chemistry – A European Journal, 2016, 22, 16974-16978
Stapled helical o-OPE foldamers as new circularly polarized luminescence emitters based on carbophilic interactions with Ag(i)-sensitivity. S. P. Morcillo, D. Miguel, L. Alvarez De Cienfuegos, J. Justicia, S. Abbate, E. Castiglioni, C. Bour, M. Ribagorda, D. J. Cardenas, J. M. Paredes, L. Crovetto, D. Choquesillo-Lazarte, A. J. Mota, M. C. Carreno, G. Longhi, J. M. Cuerva, Chem. Sci., 2016, 7, 5663-5670
Gold(I)-Catalyzed Carboaminations of Allenes by N-Allyltetrahydro-β-carbolines: An Experimental and Theoretical Study. V. Gobe, M. Dousset, P. Retailleau, V. Gandon, X. Guinchard, Advanced Synthesis & Catalysis, 2016, 358, 3960-3965
Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji-Trost reaction. X. Caumes, L. Jeanne-Julien, C. Khelifi, V. Gandon, E. Roulland, Org. Chem. Front., 2016, 3, 1462-1466
Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza-Piancatelli Reaction. D. Lebœuf, L. Marin, B. Michelet, A. Perez-Luna, R. Guillot, E. Schulz, V. Gandon, Chemistry – A European Journal, 2016, 22, 16165-16171
Catalytic applications of [IPr[middle dot]GaX2][SbF6] and related species. B. Michelet, S. Tang, G. Thiery, J. Monot, H. Li, R. Guillot, C. Bour, V. Gandon, Org. Chem. Front., 2016, 3, 1603-1613
Inverse Electron-Demand [4 + 2]-Cycloadditions of Ynamides: Access to Novel Pyridine Scaffolds. G. Duret, R. Quinlan, R. E. Martin, P. Bisseret, M. Neuburger, V. Gandon, N. Blanchard, Organic Letters, 2016, 18, 1610-1613
Synthesis of Cyclooctatetraenes through a Palladium-Catalyzed Cascade Reaction. S. Blouin, V. Gandon, G. Blond, J. Suffert, Angewandte Chemie, International Edition, 2016, 55, 7208-7211
Chiral Phosphate in Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both?. M. Barbazanges, E. Caytan, D. Lesage, C. Aubert, L. Fensterbank, V. Gandon, C. Ollivier, Chemistry - A European Journal, 2016, 22, 8553-8558
Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes. J. Ciesielski, G. Dequirez, P. Retailleau, V. Gandon, P. Dauban, Chemistry - A European Journal, 2016, 22, 9338-9347
Assessing ligand and counterion effects in the noble metal catalyzed cycloisomerization reactions of 1,6-allenynes: a combined experimental and theoretical approach. F. Jaroschik, A. Simonneau, G. Lemiere, K. Cariou, N. Agenet, H. Amouri, C. Aubert, J.-P. Goddard, D. Lesage, M. Malacria, Y. Gimbert, V. Gandon, L. Fensterbank, ACS Catalysis, 2016, 6, 5146-5160
Site-Selective Calcium-Catalyzed/Organocatalyzed Condensation of Propargyl Alcohols Tethered to β-Keto Esters. S. P. Morcillo, M. Presset, S. Floquet, V. Coeffard, C. Greck, C. Bour, V. Gandon, European Journal of Organic Chemistry, 2016, 2016, 2688-2694
Use of Planar Chiral Ferrocenylphosphine-Gold(I) Complexes in the Asymmetric Cycloisomerization of 3-Hydroxylated 1,5-Enynes. Z. Wu, P. Retailleau, V. Gandon, A. Voituriez, A. Marinetti, European Journal of Organic Chemistry, 2016, 2016, 70-75
Copper (II) triflate as additive in low loading Au(I)-catalyzed hydroalkylation of unactivated alkenes. W. Fang, M. Presset, A. Guérinot, C. Bour, S. Bezzenine-Lafollée, V. Gandon, Organic Syntheses, 2015, 92, 117-130
Chiral Calcium-BINOL Phosphate Catalyzed Diastereo- and Enantioselective Synthesis of syn-1,2-Disubstituted 1,2-Diamines: Scope and Mechanistic Studies. C. Lalli, A. Dumoulin, C. Lebee, F. Drouet, V. Guerineau, D. Touboul, V. Gandon, J. Zhu, G. Masson, Chemistry - A European Journal, 2015, 21, 1704-1712
A Terminal, Fluxional η4-Benzene Complex with a Thermally Accessible Triplet State is the Primary Photoproduct in the Intercyclobutadiene Haptotropism of (CpCo)phenylenes. T. A. Albright, R. Drissi, V. Gandon, S. Oldenhof, O. A. Oloba-Whenu, R. Padilla, H. Shen, K. P. C. Vollhardt, V. Vreeken, Chemistry - A European Journal, 2015, 21, 4546-4550
Cycloisomerization of Conjugated Trienones and Isomeric 2H-Pyrans: Unified Strategy toward Cyclopenta[b]furans. M. J. Riveira, G. N. Quiroga, E. G. Mata, V. Gandon, M. P. Mischne, Journal of Organic Chemistry, 2015, 80, 6515-6519
Double-Stereodifferentiation in Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair. M. Auge, A. Feraldi-Xypolia, M. Barbazanges, C. Aubert, L. Fensterbank, V. Gandon, E. Kolodziej, C. Ollivier, Organic Letters, 2015, 17, 3754-3757
Hypervalent-Iodine-Mediated Synthesis of 1,2-Dispirodienones: Experimental and Theoretical Investigations. T. Hromjakova, P. Retailleau, L. Grimaud, V. Gandon, L. Chabaud, C. Guillou, European Journal of Organic Chemistry, 2015, 2015, 7494-7503
CaII-Catalyzed Alkenylation of Alcohols with Vinylboronic Acids. D. Lebœuf, M. Presset, B. Michelet, C. Bour, S. Bezzenine-Lafollée, V. Gandon, Chemistry – A European Journal, 2015, 21, 11001-11005
Non-Innocent Behavior of Substrate Backbone Esters in Metal-Catalyzed Carbocyclizations and Friedel–Crafts Reactions of Enynes and Arenynes. B. Michelet, G. Thiery, C. Bour, V. Gandon, J. Org. Chem., 2015, 80, 10925-10938
New Procedures for Catalytic Carbophilic Activation by Gold and Gallium π-Acids. C. Bour, V. Gandon, Synlett, 2015, 26, 1427-1436
Gallium(III)- and calcium(II)-catalyzed Meyer-Schuster rearrangements followed by intramolecular aldol condensation or endo-Michael addition. M. Presset, B. Michelet, R. Guillot, C. Bour, S. Bezzenine-Lafollee, V. Gandon, Chem. Commun., 2015, 51, 5318-5321
First Evidence for the Existence of Hexafluoroantimonic(V) Acid. C. Bour, R. Guillot, V. Gandon, CHEMISTRY-A EUROPEAN JOURNAL, 2015, Volume: 21 Issue: 16, 6066-6069
Dibromoindium(III) cations as a pi-Lewis acid: characterization of [IPr center dot InBr2][SbF6] and its catalytic activity towards alkynes and alkenes. B. Michelet, J.-R. Colard-Itte, G. Thiery, R. Guillot, C. Bour, V. Gandon, CHEMICAL COMMUNICATIONS, 2015, Volume: 51 Issue: 34, 7401-7404