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Accueil > Les équipes > Réactivité organométallique et catalyse pour la synthèse (ROCS) > Publications

Publications

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2023



  • F. Banchini, B. Leroux, E. Le Gall, M. Presset, O. Jackowski, F. Chemla, et A. Perez-Luna, « Enantioselective Sequential Catalytic Arylation-Fukuyama Cross-coupling of 1,1-Biszincioalkane Linchpins », Chemistry – A European Journal, vol. n/a, nᵒ n/a, p. e202301084, 2023.
    Résumé : 1,1-Bis(iodozincio)alkanes are used as dinucleophilic linchpins in an enantioselective double cross-coupling reaction sequence involving aryl iodides and then thioesters. The two catalytic C−C bond-forming reactions are achieved in the same pot through two distinct palladium-based catalytic systems: a first non-enantioselective one delivering configurationally labile secondary benzylzinc species from an achiral precursor, and a second enantioconvergent one that operates a highly efficient dynamic kinetic resolution of the racemic intermediates. This strategy, new in the area of asymmetric synthesis through two consecutive electrophilic substitution reactions of geminated C(sp3)-organodimetallics, provides useful methodology to access in a modular fashion acyclic α-disubstituted ketone products with very high enantiomeric purity.
    Mots-clés : bimetallics, cross-coupling, enantioselectivity, POLE 1, ROCS, tandem reactions, zinc.
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  • G. K. Kinkutu, C. Louis, M. Roy, J. Blanchard, et J. Oble, « C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis », Beilstein Journal of Organic Chemistry, vol. 19, nᵒ 1, p. 582-592, mai 2023.
    Résumé : Beilstein Journal of Organic Chemistry
    Mots-clés : Pole 1, ROCS.
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2022



  • S. Bassoli, A. Schallmey, J. Oble, G. Poli, et A. Pradal, « Short Hydroacylation-Based Synthesis of Four Aryl-3-hydroxypropanones, Predictable Biomass-Derived C9 Platform Molecules », Catalysis Research, vol. 02, nᵒ 04, p. 036, oct. 2022.
    Résumé : A two-step protocol for the synthesis of aryl-3-hydroxypropanones, which were regarded as lignin degradation products, was proposed herein. This protocol provided a more rapid and easier access to aryl-3-hydroxypropanones, and aryl-3-hydroxypropanones were expected to be ideal platform molecules for the synthesis of more complex value-added targets.
    Mots-clés : POLE 1, ROCS.
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  • S. Curpanen, G. Poli, A. Perez-Luna, et J. Oble, « C3−H Silylation of Furfurylimines: Direct Access to a Novel Biobased Versatile Synthetic Platform Derived from Furfural », Asian Journal of Organic Chemistry, vol. 11, nᵒ 7, p. e202200199, 2022.
    Résumé : Herein we report directed iridium-catalyzed C3−H silylation of furfuryl imines, which grants access to versatile synthetic platforms. This transformation was developed on furfuryl derivatives, using imines as directing groups, and trialkylsilanes or bis(trimethylsilyl)methylsilane as silylating agents, in the presence of a hydride scavenger. Subsequently, fluoride-mediated activation strategies were applied to the C3−SiMe(OSiMe3)2 furfural derivatives to achieve a wide range of transformations of the C3−Si bond. Arylation, alkenylation, alkynylation, allylation and alkylation, as well as halogenation and trifluoromethylation were achieved in modest to high yields. A variety of high value-added products were thus easily obtained from the same common C3-silylated furfural-based platform.
    Mots-clés : Biomass, Fluoride, Furfural, Iridium, POLE 1, ROCS, Silicon.
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  • S. Curpanen, P. Reichert, G. Lupidi, G. Poli, J. Oble, et A. Perez-Luna, « Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization », Beilstein Journal of Organic Chemistry, vol. 18, nᵒ 1, p. 1256-1263, sept. 2022.
    Résumé : Beilstein Journal of Organic Chemistry
    Mots-clés : POLE 1, ROCS.
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  • S. Gahlot, A. Gradone, M. Roy, M. Giorgi, S. Conti, P. Ceroni, M. Villa, et M. Gingras, « Persulfurated Benzene-Cored Asterisks with π-Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties », Chemistry – A European Journal, vol. 28, nᵒ 46, p. e202200797, 2022.
    Résumé : The synthesis of regioisomeric asterisks (5) and (6) incorporating a benzene core with six 1-naphthylthio or six 2-naphthylthio arms are reported in search for new materials with optoelectronic properties. The consequences on the extension of a π system surrounding a persulfurated benzene core provide a new avenue to study the structural, photophysical, and chemical properties of such family of all-organic phosphors. It also diverts the persulfuration mechanism after two radical cyclizations for making a [5]dithiohelicene by-product (7) and favors dynamic sulfur component exchange reactions surrounding the core. These exchanges convert asterisks (5) and (6), non-phosphorescent at 20 °C to the highly phosphorescent (4) (ϕ ∼100 %, solid state at 20 °C). For asterisks (5) and (6), the absence of the typical phosphorescence of the per(phenylthio)benzene core in the solid state at 20 °C and the presence of a weak naphthalene-based phosphorescence at 77 K is attributed to an energy transfer from the triplet state of the persulfurated benzene core to the outer naphthalene moieties, resulting in an antenna system.
    Mots-clés : arenes, aromatic substitution, materials science, photophysics, POLE 1, ROCS, sulfur, supramolecular chemistry.
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  • O. Jackowski et A. Perez-Luna, « 4.4.38.14 Propargylsilanes (Update 2022) », in Science of Synthesis, 2022/3: Knowledge Updates 2022/3, 1st editionᵉʳ éd., Thieme Verlag, 2022.
    Résumé : Thieme E-Books & E-Journals
    Mots-clés : POLE 1, ROCS.
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  • C. Loro, J. Oble, F. Foschi, M. Papis, E. M. Beccalli, S. Giofrè, G. Poli, et G. Broggini, « Acid-mediated decarboxylative C–H coupling between arenes and O-allyl carbamates », Organic Chemistry Frontiers, vol. 9, nᵒ 6, p. 1711-1718, mars 2022.
    Résumé : Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)2 or TMSOTf as promoters affords N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter and of the aryl substrates. A full mechanistic rational allowing appreciation of the outcome of these novel C–H based cascades is proposed. An initial acid promoted decarboxylative/deamidative Friedel–Crafts allylation takes place. After protonation of the allylated arene, evolution of the resulting cation may follow different paths depending on the nature of the arene partner and of the allyl moiety in the carbamate.
    Mots-clés : POLE 1, ROCS.
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  • A. Mori, S. Curpanen,

    C. Pezzetta, A. Perez-Luna, G. Poli, et J. Oble, « C−H Activation Based Functionalization of Furfural Derivatives », European Journal of Organic Chemistry, vol. 2022, nᵒ 43, p. e202200727, 2022.
    Résumé : Furfural and related compounds are building blocks of industrial interest, obtained from raw biomass. Their use as precursors of basic and fine chemicals has gained increasing attention as a green alternative to petroleum-derived compounds. Several works have reported the functionalization of furfurals to obtain a wider range of chemicals, opening up new synthetic possibilities and applications, ranging from biofuels to pharmaceuticals. Among these works, processes based on C−H activation are the most attractive ones for their atom economy and the possibility to use non-activated substrates. This minireview summarizes the reported methods of direct C−H functionalization of furfurals without prior modification of the redox state of the aldehyde function. In particular, the transition metal catalyzed functionalization of each bond of the heteroaromatic nucleus of these molecules is systematically discussed, as well as examples of C−H transformations of the aldehyde function.
    Mots-clés : Biomass, Catalysis, C−H Activation, Furfural, POLE 1, ROCS, Transition metal.
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  • A. Pradal, « 2.15 - Four-Membered Rings With Two Oxygen Atoms », in Comprehensive Heterocyclic Chemistry IV, D. S. C. Black, J. Cossy, et C. V. Stevens, Éd. Oxford: Elsevier, 2022, p. 507-537.
    Résumé : This chapter is dealing with the chemistry about 1,2- and 1,3-dioxetanes, even if most of what is reported concerns 1,2-dioxetane derivatives. These derivatives are becoming more and more important since their chemiluminescent properties are of great interest for imaging and detection applications. After a description of the theoretical studies made for a better understanding of the decomposition mechanism, some new data dealing with analytics and synthesis are given. This chapter ends with new updates about applications of the chemistry of 1,2-dioxetanes.
    Mots-clés : Chemiluminescence, Decomposition, Dioxetanes, Firefly dioxetanone, Light emission, POLE 1, ROCS.
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  • M. Roy et M. Gingras, « Multihelicenic Platforms from Halogenated Helicenes and Related Precursors », in Helicenes, John Wiley & Sons, Ltd, 2022, p. 263-282.
    Résumé : New helicenes and helicenic platforms have been florishing in the last few years. This is mainly due to the search for exalted chiroptical properties from novel chiral carbon architectures, nanoribbons and nanographenes, in view of their potent uses as chiral building blocks in optoelectronic and photovoltaic devices, in sensors, in molecular electronics, or as polymeric materials and synthons in chiral materials science. Thus, π-extension of the helicene skeleton has been investigated in several directions, but a major challenge remains the configurational stability of the structure. This challenge has been taken up by the synthesis of multihelicenes, which could be configurationally stable. In this chapter, we focus on several approaches for making stable multihelicenes from halogenated helicenes and their related precursors, by using metal-catalyzed reactions: Suzuki–Miyaura, Heck, and some cyclotrimerization reactions. An emphasis is made on the use of the Ni(0)-assisted cyclotrimerization reactions for making multihelicenic platforms.
    Mots-clés : chiral nanographenes, halogenated helicenes, Heck couplings, multihelicenes, Ni(0) cyclotrimerizations, POLE 1, ROCS, Suzuki–Miyaura couplings.
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2020



  • Y. Liu, J. Oble, A. Pradal, et G. Poli, « Catalytic Domino Annulations through η3-Allylpalladium Chemistry: A Never-Ending Story », European Journal of Inorganic Chemistry, vol. 2020, nᵒ 11-12, p. 942-961, 2020.
    Résumé : Annulative η3-allylpalladium chemistry has been a longstanding trending research topic since the 80's. Nowadays, this research area is still providing challenges to the catalysis community leading to the development original and brand-new transformations. Several reaction partners have been used as precursors for η3-allylpalladium species, namely allyl diacetates, allyl monoacetates, 3-acetoxy-2-trimethylsilylmethyl-1-propene (ASMP), alkylidene cyclopropanes (ACPs), vinyl cyclopropanes (VCPs), vinyl aziridines, and vinyl epoxides. This minireview is intended to show the recent developments in the field of annulative η3-allylpalladium chemistry with emphasis on new reactivity, enantioselective transformations as well as potential applications in total synthesis.
    Mots-clés : POLE 1, ROCS.
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2018


  • F. Chemla, F. Fuster, H. Gérard, A. Markovits, A. Naitabdi, et R. Vuilleumier, « Un laboratoire pédagogique à grande échelle: les ateliers bidisciplinaires », L'Actualité Chimique, nᵒ 433, 2018.
    Résumé : Un enseignement bidisciplinaire obligatoire a été mis en place en première année de licence, basé sur la réalisation en petits groupes de projets en
    Mots-clés : POLE 1, ROCS.
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  • C. Pezzetta, S. Tshepelevitsh, I. Leito, et G. Poli, « Comment on “Zemplén transesterification: a name reaction that has misled us for 90 years” by B. Ren, M. Wang, J. Liu, J. Ge, X. Zhang and H. Dong, Green Chemistry, 2015, 17, 1390–1394 », Green Chemistry, vol. 20, nᵒ 10, p. 2392-2394, mai 2018.
    Résumé : The recent title paper reports that the Zemplén transesterification can be accomplished equally well using catalytic amounts of NaOH in MeOH instead of the classical catalytic amounts of MeONa in dry MeOH, which led the authors to propose a modified mechanism for this transformation. Simple proton transfer considerations show that, in the above modified conditions, the original methoxy anion-catalysed mechanistic path still holds against the proposed hydroxy anion-catalysed one, when hydrogen bonding is taken into account.
    Mots-clés : POLE 1, ROCS.
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2017



  • M. Beaupérin, D. Polat, F. Roudesly, S. Top, A. Vessières, J. Oble, G. Jaouen, et G. Poli, « Approach to ferrocenyl-podophyllotoxin analogs and their evaluation as anti-tumor agents », Journal of Organometallic Chemistry, vol. 839, p. 83-90, juin 2017.
    Résumé : Podophyllotoxin is a natural product endowed of a high antimitotic activity and a high affinity for tubulin. Its action results in the cessation of cell division, inducing cell death. However, its high toxicity restrains its use as drug. To overcome this drawback, several chemical modifications of the native podophyllotoxin have been made. However, to date, no reports have so far been directed toward incorporation of a metallocene moiety. The search for new organometallic drugs is a central field in drug discovery, including the domain of cancer therapy. In particular, metallocenyl moieties are known to increase or decrease, depending on the degree of conjugation in the organometallic motif, the selectivity of drugs toward cancer cells. The conjugate organometallic compound reduces the damage of healthy tissues, yet permitting the selective desired antimitotic and cytotoxic effects of the active principle. We report here the synthesis of ferrocene-containing podophyllotoxin analogs and preliminary antiproliferative tests.
    Mots-clés : Antitumor agent, Bioorganometallic chemistry, CHEMBIO, Ferrocene, Multi-step synthesis, Palladium, Podophyllotoxin, POLE 1, POLE 3, ROCS.
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