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

Publications

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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.


  • 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.


  • 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.


  • 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.


  • 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. n/a, nᵒ n/a, 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.


  • 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.


  • 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.

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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