Maxime R. Vitale


EDUCATION

June 2016                           Habilitation à diriger des recherches, Pierre & Marie Curie University (Paris VI)

Title: “Metal Catalysis and Metal/Organo Synergistic Catalysis

Defended on June 13th 2016 in front of the jury composed of : Prof. M. Malacria (Chair), Prof. D. J. Dixon (Reviewer), Dr. F. Leroux (Reviewer), Dr. L. Micouin (Examinator), Dr. V. Michelet (Examinator), Dr. V. Vidal (Examinator). Mention Très Honorable

Sept. 2004                          PhD in Organic Chemistry, Pierre & Marie Curie University (Paris VI)

Title : “Synthèse d’analogues de la podophyllotoxine par une nouvelle séquence palladocatalysée : alkylation allylique – couplage de Hiyama.

Defended on september 28th 2004 dn front of the jury composed of :Pr. L. Fensterbank (Chair), Pr. J.-C. Fiaud (Reviewer), Pr. H.-P. Husson (Reviewer), Dr. D. Lesuisse (Examinator), Pr. G. Poli (Examinator), Dr. G. Prestat (Examinator). Mention Très Honorable

2000 – 2001                        Master in Organic and Bio-organic Chemistry, Pierre & Marie Curie University (Paris VI)


POSITIONS

2019                CNRS Researcher at the ENS Paris – UMR 7203

2008                      CNRS Researcher at Chimie ParisTech

2007                      Post-doctoral research associate at Chimie ParisTech
(under the supervision of Dr V. Michelet)

2006                      Post-doctoral research associate at the University von Amsterdam
(under the supervision of Prof J. van Maarseveen)

2004-2005             Post-doctoral research associate at the University of Bristol
(under the supervision of Prof V. K. Aggarwal)


RESEARCH INTERESTS

Catalysis : Metal Catalysis, Organocatalysis, Synergistic Catalysis

Electrosynthesis, Photoredox Catalysis

Isocyanide-based Multicomponent Reactions

Mechanistic studies, Physical Organic Chemistry


PUBLICATIONS

[41]A Mn(OAc)3 Triggered Formation of Cyclopropanes from Ugi Adducts. El Kaim, L.; Grimaud, L.; Vitale, M.; Cheibas, C.; Vieu-Tota, E.; Casaretto, N. Synlett 2023, ASAP, doi :10.1055/a-2005-5220.
[40]*Electrochemical Benzylic C–H Functionalization with Isocyanides. Tang, S.; Guillot, R.; Grimaud, L.;* Vitale, M. R.;* Vincent, G. Org. Lett. 2022, 24, 2125–2130.
[39]Redox Control of Particle Deposition from Drying Drops. Galy, P. E.; Guitton-Spassky, T.; Sella, C.; Thouin, L.; Vitale, M. R.; Baigl, D.* ACS Appl. Mater. Interfaces 2022, ACS Appl. Mater. Interfaces 2022, 14, 3374–3384.
[38]Iron(II)-Catalyzed Intermolecular Aziridination of Alkenes Employing Hydroxylamine Derivatives as Clean Nitrene Sources. Kirby, G.; Grimaud, L.; Vitale, M. R.; Prestat, G.;* Berhal, F.* Green Chem. 2021, 23, 9428–9432.
[37]*Electrochemical TEMPO-Catalyzed Oxidative Ugi-Type Reaction. Pan, N.; Xinen Lee, M.; Bunel, L.; Grimaud, L.;* Vitale, M. R.* ACS Organic & Inorganic Au 2021,1, 18–22.
[36]Role of dppf Monoxide in the Transmetalation Step of the Suzuki–Miyaura Coupling Reaction. Payard, P.-A.;* Bohn, A.; Tocqueville, D.; Jaouadi, K.; Escoude, E.; Ajig, S.; Dethoor, A.; Gontard, G.; Perego, L. A.; Vitale, M.; Ciofini, I.;* Wagschal, S.;* Grimaud, L.* Organometallics 2021, 40, 1120–1128.
[35]Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines. Lyu, J.; Claraz, A.; Vitale, M. R.; Allain, C.; Masson, G.* J. Org. Chem. 2020, 85, 12843–12855.
[34]*Copper(I)-Catalyzed Dearomative (3+2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to Cyclopenta[b]Indolines. Ling, J.; Mara, D.; Roure, B.; Laugeois, M.; Vitale, M. R.* J. Org. Chem. 2020, 85, 3838–3848.
[33]Cyclopropyl Thioethers, New Inputs for Palladium Catalyzed Ring Opening of Cyclopropanes. Ponra, S.; Nyadanu, A.; Pan, N.; Martinand-Lurin, E.; Savy, A.; Vitale, M. R.; El Kaim, L.* and Grimaud, L.* Org. Process Res. Dev. 2020, 24, 827–834.
[32]*Electrochemical TEMPO-catalyzed multicomponent C(sp3)–H α-carbamoylation of free cyclic secondary amines.
Pan, N.; Ling, J.; Zapata, R.; Pulicani, J.-P.; Grimaud, L.;* Vitale, M. R.* Green Chem. 2019, 21, 6194–6199.
 
[31]*Palladium(0)-Catalyzed Diastereoselective (3+2) Cycloadditions of Vinylcyclopropanes with Sulfonyl-Activated Imines. Ling, J.; Laugeois, M.; Ratovelomanana-Vidal, V.; Vitale, M. R.* Synlett 2018, 29, 2288–2292.
[30]*Palladium(0)-Catalyzed Dearomatization of 2-Nitrobenzofurans Through Formal (3+2) Cycloadditions with Vinylcyclopropanes: a Straightforward Access to Cyclopenta[b]benzofurans. Ling, J.; Laugeois, M.; Michelet, V.; Ratovelomanana-Vidal, V.; Vitale, M. R.* Synlett 2018, 29, 928–932.
[29]*TiCl4-Mediated Synthesis of 3,4-Hetero-Disubstituted Isocoumarins by Means of Isocyanide Insertion Reactions. Ponra, S.; Nyadanu, A.; El-Kaïm, L.;* Grimaud, L.;* Vitale, M. R.* Synthesis 2018, 50, 1331–1342.
[28]*Palladium(0)-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined 2,3-Fused Cyclopentannulated Indoline Derivatives. Laugeois, M.; Ling, J.; Ferard, C.; Michelet, V.; Ratovelomanana-Vidal, V.; Vitale, M. R.* Org. Lett. 2017, 19, 2266–2269.
[27]*TiCl4-Mediated Preparation of Thiophthalide Derivatives via Formal Thio-Passerini Reactions. Ponra, S.; Nyadanu, A.; El-Kaïm, L.;* Grimaud, L.;* Vitale, M. R.* Org. Lett. 2016, 18, 4060–4063.
[26]*Asymmetric preparation of polysubstituted cyclopentanes by synergistic Pd(0)/amine catalyzed formal [3+2] cycloadditions of vinyl cyclopropanes with enals. Laugeois, M.; Ponra, S.; Ratovelomanana-Vidal, V.,* Michelet, V.;* Vitale, M. R.* Chem. Commun. 2016, 52, 5332-5335.
[25]*Practical synthesis of polysubstituted naphthalene derivatives via HNTf2-catalyzed benzannulation reaction. Ponra, S.; Vitale, M. R.;* Michelet, V.;* Ratovelomanana-Vidal, V.* Arkivoc 2016, (ii), 62–81.
[24]*HNTf2-Catalyzed Regioselective Preparation of Polysubstituted Naphthalene Derivatives Through Alkyne-Aldehyde Coupling. Ponra, S.; Vitale, M. R.;* Michelet, V.;* Ratovelomanana-Vidal, V.* J. Org. Chem. 2015, 80, 3250–3257.
[23]Synergistic Iron-and Amine-Catalysis in Carbocyclizations. Praveen, C.; Leveque, S.; Vitale, M. R.; Michelet,* V.; Vidal,* V. Synthesis 2014, 46, 1334–1338.
[22]Enantioselective Merger of Aminocatalysis with π-Lewis Acid Metal Catalysis: Asymmetric Preparation of Carbo- and Heterocycles. Praveen, C.; Montaignac, B.; Vitale, M. R.; Ratovelomanana-Vidal, V.;* Michelet, V.* ChemCatChem 2013, 5, 2395–2304.
[21]Iridium(III)-Catalyzed Approach for the Synthesis of Fused Arenes: Access to Isoindolines, Indanes, and Dihydroisobenzofurans. Auvinet, A.-L.; Ez-Zoubir, M.; Bompard, S.; Vitale, M. R.; Brown, J. A.; Michelet, V.;* Ratovelomanana-Vidal, V.* ChemCatChem 2013, 5, 2389–2394.
[20]New Advances in Bis(Sulfoxides) Chemistry. Beauvière, S.; Brebion, F.; Chelli, S.; Delouvrié, B.; Gomez, C.; Kwasnieski, O.; Mallorquin, R.-M.; Najera, F.; Vincent, G.; Vitale, M.; Derat, E.; Marek, I.; Malacria, M.; Goddard, J.-P.; Fensterbank, L.* Phosphorus, Sulfur, and Silicon 2013, 188, 367–376.
[19]Practical and Efficient Iridium Catalyst for Benzannulation: An Entry To Isoindolines. Auvinet, A.-L.; Ez-Zoubir, M.; Vitale, M. R.; Brown, J. A.; Michelet, V.;* Ratovelomanana-Vidal, V.* ChemSusChem 2012, 5, 1888–1891.
[18]Enantioselective metallo-organocatalyzed preparation of cyclopentanes bearing an all-carbon quaternary stereocenter. Montaignac, B.; Praveen, C.; Vitale, M. R.; Michelet, V.;* Ratovelomanana-Vidal, V.* Chem. Commun. 2012, 48, 6559–6561.
[17]Copper(I)-amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems. Montaignac, B.; Ostlund, V.; Vitale, M. R.; Ratovelomanana-Vidal, V.;* Michelet, V.* Org. Biomol. Chem. 2012, 10, 2300–2306.
[16]Asymmetric Au-catalyzed domino cyclization/nucleophile addition reactions of enynes in the presence of water, methanol and electron-rich aromatic derivatives. Pradal, A.; Chao, C.-M.; Vitale, M. R.; Toullec, P. Y.; Michelet, V.* Tetrahedron 2011, 67, 4371–4377.
[15]Cooperative Copper(I) and Primary Amine Catalyzed Room-Temperature Carbocyclization of Formyl Alkynes. Montaignac, B.; Vitale, M. R.; Ratovelomanana-Vidal, V.;* Michelet, V.* Eur. J. Org. Chem. 2011, 3723–3727.
[14]InCl3/CyNH2 Cocatalyzed Carbocyclization Reaction: An Entry to α-Disubstituted exo-Methylene Cyclopentanes. Montaignac, B.; Vitale, M. R.; Ratovelomanana-Vidal, V.;* Michelet, V.* J. Org. Chem. 2010, 75, 8322–8325.
[13]Combined InCl3– and Amine-Catalyzed Intramolecular Addition of α-Disubstituted Aldehydes onto Unactivated Alkynes. Montaignac, B.; Vitale, M. R.; Michelet, V.;* Ratovelomanana-Vidal, V.* Org. Lett. 2010, 12, 2582–2585.
[12]Chiral undecagold clusters: synthesis, characterization and investigation in catalysis. Andreiadis, E. S.; Vitale, M. R.; Mézailles,* N; Le Goff, X.; Le Floch, P.; Toullec, P. Y.;* Michelet, V.* Dalton Trans. 2010, 39, 10608–10616.
[11]Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions. Chao, C.-M.; Vitale, M. R.; Toullec, P. Y.; Genêt, J.-P.; Michelet, V.* Chem. Eur. J. 2009, 15, 1319–1323.
[10]Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2-and 1,3-Diols and 1,2,4-Triols. Vedrenne, E.; Wallner, O. A.; Vitale, M.; Schmidt, F.; Aggarwal, V. K.* Org. Lett. 2009, 11, 165–168.
[9]New picropodophyllin analogs via palladium-catalyzed allylic alkylation – Hiyama cross-coupling sequences. Vitale, M.; Prestat, G.;* Lopes, D.; Madec, D.; Kammerer, C.; Poli, G.;* Girnita, L. J. Org. Chem. 2008, 73, 5795–5805.
[8]Pseudo-domino palladium-catalyzed allylic alkylation/Mizoroki–Heck coupling reaction: a key sequence toward (±)-podophyllotoxin. Mingoia, F.; Vitale, M.; Madec, D.;* Prestat, G.; Poli, G.* Tetrahedron Lett. 2008, 49, 760–763.
[7]An Aptly Positioned Azido Group in the Spacer of a Protein Cross-Linker for Facile Mapping of Lysines in Close Proximity. Kasper, P.T.; Back, J.W.; Vitale, M.; Hartog, A.F; Roseboom, W.; de Koning, Leo J.; van Maarseveen, J.H.; Muijsers, A.O.; de Koster, C.G.; de Jong, L.* ChemBioChem 2007, 8, 1281–1292.
[6]Ligand-Induced Control of C-H versus Aliphatic C-C Migration Reactions of Rh Carbenoids. Vitale, M.; Lecourt, T.; Sheldon, C. G.; Aggarwal, V. K.* J. Am. Chem. Soc. 2006, 128, 2524–2525.
[5]A Palladium-Catalyzed Sequence of Allylic Alkylation and Hiyama Cross-Coupling: Convenient Synthesis of 4-(α-Styryl) γ-Lactones. Vitale, M.; Prestat, G.; Lopes, D.; Madec, D.; Poli, G.* Synlett 2006, 14, 2231–2234.
[4]Diastereoselective Preparation of Silylated Pyrrolidones through Palladium-Catalysed Cyclizations. Thorimbert, S.; Giambastiani, G.; Commandeur, C.; Vitale, M.; Poli, G.;* Malacria, M.* Eur. J. Org. Chem. 2003, 2702–2708.
[3]Enantiopure alkylidene-1,1-bis-p-tolylsulfoxides as new partners in diastereoselective radical cyclizations. Brebion, F.; Vitale, M.; Fensterbank, L.;* Malacria, M.* Tetrahedron: Asymmetry 2003, 14, 2889–2896.
[2]Rationalizing Ring-Size Selectivity in Intramolecular Pd-Catalyzed Allylations of Resonance-Stabilized Carbanions. Norrby, P.-O.;* Mader, M. M.; Vitale, M.; Prestat, G.; Poli, G.* Organometallics 2003, 22, 1849–1855.
[1]Alkylation of active methylenes via benzhydryl cations. Bisaro, F.; Prestat, G.; Vitale, M.; Poli, G.* Synlett 2002, 11, 1823–1826.