SysChem Complex Systems Chemistry
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Student Publications Arising from

Research at the Graduate School

42

publications since 2018

Featured publications

E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing

The synthesis of therapeutic macrocyclic trisubstituted alkenes faces inefficiency. A potential solution, catalytic macrocyclic ring-closing metathesis, has limitations. This study introduces a new method for creating diverse trisubstituted macrocyclic olefins, overcoming challenges like alkene isomerization. The method's effectiveness is showcased through examples, including altering selectivity in macrolactam formation and synthesizing the cytotoxic natural product dolabelide C.

Diastereo- and enantioselective synthesis of compounds with a trifluoromethyl- and fluoro-substituted carbon centre

Fluorine-containing molecules are vital in drug discovery. Current methods can selectively synthesize specific organofluorine compounds, but those with both trifluoromethyl and fluoro-substituted stereogenic carbon centers are rare. This study introduces a catalytic approach to create such compounds, using a polyfluoroallyl boronate and an in situ-formed organozinc complex. This method enables diverse synthesis and reveals unexpected reactivity patterns due to the unique carbon site. The potential impact is highlighted through the preparation of tetrafluoro-monosaccharides, including analogs of the antiviral drug sofosbuvir.

List of publications since 2018:

The contribution of master's and PhD students is indicated in red.

  • Bachir, A.; Ciocchetti, F.; Couto, D. P.; Di Noja, S.; Pezzato, C.; Ragazzon, G. Photochemical Bromination of 2,5-Dimethylbenzoic Acid as Key Step of an Improved Alkyne-Functionalized Blue Box Synthesis. European Journal of Organic Chemistry 2023, 26 (29). DOI: 10.1002/ejoc.202300498.
  • Lainer, B.; Das, K.; Dydio, P. Variable structure diversification by multicatalysis: the case of alcohols. Chemical Communications 2023, 59 (32), 4716-4725. DOI: 10.1039/d3cc00551h.
  • Martinez, G.; Avila-Rovelo, N. R.; Carmona-Vargas, C. C.; Id-boubrik, I.; Ruiz-Carretero, A. Alternative Functionalization of Hydrogen-Bonded Diketopyrrolopyrrole Derivatives. European Journal of Organic Chemistry 2023. DOI: 10.1002/ejoc.202300344.
  • Muller, C.; Horky, F.; Vayer, M.; Golushko, A.; Leboeuf, D.; Moran, J. Synthesis of functionalised isochromans: epoxides as aldehyde surrogates in hexafluoroisopropanol. Chemical Science 2023. DOI: 10.1039/d2sc06692k.
  • Piejko, M.; Patrahau, B.; Joseph, K.; Muller, C.; Devaux, E.; Ebbesen, T. W.; Moran, J. Solvent Polarity under Vibrational Strong Coupling. Journal of the American Chemical Society 2023, 145 (24), 13215-13222. DOI: 10.1021/jacs.3c02260.
  • Pozhydaiev, V.; Vayer, M.; Fave, C.; Moran, J.; Leboeuf, D. Synthesis of Unprotected beta-Arylethylamines by Iron(II)-Catalyzed 1,2-Aminoarylation of Alkenes in Hexafluoroisopropanol. Angewandte Chemie-International Edition 2023. DOI: 10.1002/anie.202215257.
  • Ritacca, A. G.; Falcone, E.; Doumi, I.; Vileno, B.; Faller, P.; Sicilia, E. Dual Role of Glutathione as a Reducing Agent and Cu-Ligand Governs the ROS Production by Anticancer Cu-Thiosemicarbazone Complexes. Inorganic Chemistry 2023, 62 (9), 3957-3964. DOI: 10.1021/acs.inorgchem.2c04392.
  • Samokhvalova, S.; Lutz, J. F. Macromolecular Information Transfer. Angewandte Chemie-International Edition 2023. DOI: 10.1002/anie.202300014.
  • Aleksandrova, M.; Bonfio, C. Bioenergetics of early life. Embo Reports 2022, 23 (8). DOI: 10.15252/embr.202255679.
  • Avila-Rovelo, N. R.; Martinez, G.; Matsuda, W.; Sinn, S.; Leveque, P.; Schwaller, D.; Mesini, P.; Seki, S.; Ruiz-Carretero, A. Hydrogen-Bonded Organic Semiconductors with Long Charge Carrier Lifetimes. Journal of Physical Chemistry C 2022, 126 (26), 10932-10939. DOI: 10.1021/acs.jpcc.2c03105.
  • Casciuc, I.; Osypenko, A.; Kozibroda, B.; Horvath, D.; Marcou, G.; Bonachera, F.; Varnek, A.; Lehn, J. M. Toward in Silico Modeling of Dynamic Combinatorial Libraries. Acs Central Science 2022, 8 (6), 804-813. DOI: 10.1021/acscentsci.2c00048.
  • Martinez, S.; Dydio, P. Density Functional Theory Studies of the Catalyst Structure-Activity and Selectivity Relationships in Rh(I)-Catalyzed Transfer C-H Borylation of Alkenes. Organometallics 2022, 41 (13), 1649-1658. DOI: 10.1021/acs.organomet.2c001481649Organometallics2022.
  • Mu, Y. C.; Hartrampf, F. W. W.; Yu, E. C.; Lounsbury, K. E.; Schrock, R. R.; Romiti, F.; Hoveyda, A. H. E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing. Nature Chemistry 2022, 14 (6), 640-+. DOI: 10.1038/s41557-022-00935-y.
  • Shoueir, K.; Mohanty, A.; Janowska, I. Industrial molasses waste in the performant synthesis of few-layer graphene and its Au/Ag nanoparticles nanocomposites. Photocatalytic and supercapacitance applications. Journal of Cleaner Production 2022, 351. DOI: 10.1016/j.jclepro.2022.131540.
  • Xu, S. B.; del Pozo, J.; Romiti, F.; Fu, Y.; Mai, B. K.; Morrison, R. J.; Lee, K. A.; Hu, S. W.; Koh, M. J.; Lee, J. H.; et al. Diastereo- and enantioselective synthesis of compounds with a trifluoromethyl- and fluoro-substituted carbon centre. Nature Chemistry 2022, 14 (12), 1459-+. DOI: 10.1038/s41557-022-01054-4.
  • Zeidan, N.; Bicic, S.; Mayer, R. J.; Leboeuf, D.; Moran, J. Hydroarylation of enamides enabled by HFIP via a hexafluoroisopropyl ether as iminium reservoir. Chemical Science 2022, 13 (28), 8436-8443. DOI: 10.1039/d2sc02012b.
  • Baybekov, S.; Marcou, G.; Ramos, P.; Saurel, O.; Galzi, J. L.; Varnek, A. DMSO Solubility Assessment for Fragment-Based Screening. Molecules 2021, 26 (13). DOI: 10.3390/molecules26133950.
  • Carmona-Vargas, C. C.; Giuseppone, N. Template-Directed Synthesis of Redox-Active c3 Daisy Chain Rotaxanes. Chem 2021, 7 (1), 11-13. DOI: 10.1016/j.chempr.2020.12.008.
  • Casnati, A.; Lichosyt, D.; Lainer, B.; Veth, L.; Dydio, P. Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols. Organic Letters 2021, 23 (9), 3502-3506. DOI: 10.1021/acs.orglett.1c00939.
  • Chatelain, P.; Muller, C.; Sau, A.; Brykczynska, D.; Bahadori, M.; Rowley, C. N.; Moran, J. Desulfonative Suzuki-Miyaura Coupling of Sulfonyl Fluorides. Angewandte Chemie-International Edition 2021, 60 (48), 25307-25312. DOI: 10.1002/anie.202111977.
  • Falcone, E.; Okafor, M.; Vitale, N.; Raibaut, L.; Sour, A.; Faller, P. Extracellular Cu2+ pools and their detection: From current knowledge to next-generation probes. Coordination Chemistry Reviews 2021, 433. DOI: 10.1016/j.ccr.2020.213727.
  • Falcone, E.; Vileno, B.; Hoang, M.; Raibaut, L.; Faller, P. A luminescent ATCUN peptide variant with enhanced properties for copper(II) sensing in biological media. Journal of Inorganic Biochemistry 2021, 221. DOI: 10.1016/j.jinorgbio.2021.111478.
  • Garcia, A. M.; Martinez, G.; Ruiz-Carretero, A. The Importance of Spin State in Chiral Supramolecular Electronics. Frontiers in Chemistry 2021, 9. DOI: 10.3389/fchem.2021.722727.
  • Garcia, A. M.; Martinez, G.; Ruiz-Carretero, A. The Importance of Spin State in Chiral Supramolecular Electronics. Frontiers in Chemistry 2021, 9. DOI: 10.3389/fchem.2021.722727.
  • Giaveri, S.; Schmitt, A. M.; Julia, L. R.; Scamarcio, V.; Murello, A.; Cheng, S. Y.; Menin, L.; Ortiz, D.; Patiny, L.; Bolisetty, S.; et al. Nature-Inspired Circular-Economy Recycling for Proteins: Proof of Concept. Advanced Materials 2021, 33 (44). DOI: 10.1002/adma.202104581.
  • Lainer, B.; Lichosyt, D.; Aleksandrova, M.; Dydio, P. Enantioselective alpha-Arylation of Primary Alcohols under Sequential One-Pot Catalysis. Journal of Organic Chemistry 2021, 86 (13), 9253-9262. DOI: 10.1021/acs.joc.1c00983.
  • Lainer, B.; Lichosyt, D.; Aleksandrova, M.; Dydio, P. Enantioselective alpha-Arylation of Primary Alcohols under Sequential One-Pot Catalysis. Journal of Organic Chemistry 2021, 86 (13), 9253-9262. DOI: 10.1021/acs.joc.1c00983.
  • Martinez, S.; Veth, L.; Lainer, B.; Dydio, P. Challenges and Opportunities in Multicatalysis. Acs Catalysis 2021, 11 (7), 3891-3915. DOI: 10.1021/acscatal.0c05725.
  • Mohanty, A.; Viet, C. D.; Roger, A. C.; Adam, A.; Mertz, D.; Baaziz, W.; Janowska, I. Structural impact of carbon nanofibers/few-layer-graphene substrate decorated with Ni for CO2 methanation via inductive heating. Applied Catalysis B-Environmental 2021, 298. DOI: 10.1016/j.apcatb.2021.120589.
  • Vazquez, A. G.; Rodriguez-Luna, M. R.; Verde, J.; Piantanida, E.; Alonci, G.; Palermo, M.; Serra, E.; De Cola, L.; Gimenez, M. E. Image-Guided Surgical Simulation in Minimally Invasive Liver Procedures: Development of a Liver Tumor Porcine Model Using a Multimodality Imaging Assessment. Journal of Laparoendoscopic & Advanced Surgical Techniques 2021, 31 (10), 1097-1103. DOI: 10.1089/lap.2021.0105.
  • Zhang, S. F.; Vayer, M.; Noel, F.; Vukovic, V. D.; Golushko, A.; Rezajooei, N.; Rowley, C. N.; Leboeuf, D.; Moran, J. Unlocking the Friedel-Crafts arylation of primary aliphatic alcohols and epoxides driven by hexafluoroisopropanol. Chem 2021, 7 (12), 3425-3441. DOI: 10.1016/j.chempr.2021.10.023.
  • Falcone, E.; Ahmed, I. M. M.; Oliveri, V.; Bellia, F.; Vileno, B.; El Khoury, Y.; Hellwig, P.; Faller, P.; Vecchio, G. Acrolein and Copper as Competitive Effectors of alpha-Synuclein. Chemistry-a European Journal 2020, 26 (8), 1871-1879. DOI: 10.1002/chem.201904885.
  • Falcone, E.; Gonzalez, P.; Lorusso, L.; Seneque, O.; Faller, P.; Raibaut, L. A terbium(iii) luminescent ATCUN-based peptide sensor for selective and reversible detection of copper(ii) in biological media. Chemical Communications 2020, 56 (35), 4797-4800. DOI: 10.1039/d0cc01007c.
  • Morrison, R. J.; van der Mei, F. W.; Romiti, F.; Hoveyda, A. H. A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing a Z-Alkenyl Chloride or Trifluoromethyl Group. A Concise and Protecting Group-Free Synthesis of Mycothiazole. Journal of the American Chemical Society 2020, 142 (1), 436-447. DOI: 10.1021/jacs.9b11178.
  • Pomplun, S.; Shugrue, C. R.; Schmitt, A. M.; Schissel, C. K.; Farquhar, C. E.; Pentelute, B. L. Secondary Amino Alcohols: Traceless Cleavable Linkers for Use in Affinity Capture and Release. Angewandte Chemie-International Edition 2020, 59 (28), 11566-11572. DOI: 10.1002/anie.202003478.
  • Reina, G.; Peng, S. Y.; Jacquemin, L.; Andrade, A. F.; Bianco, A. Hard Nanomaterials in Time of Viral Pandemics. Acs Nano 2020, 14 (8), 9364-9388. DOI: 10.1021/acsnano.0c04117.
  • Singh, N.; Lainer, B.; Formon, G. J. M.; De Piccoli, S.; Hermans, T. M. Re-programming Hydrogel Properties Using a Fuel-Driven Reaction Cycle. Journal of the American Chemical Society 2020, 142 (9), 4083-4087. DOI: 10.1021/jacs.9b11503.
  • Van der Schueren, B.; El Marouazi, H.; Mohanty, A.; Leveque, P.; Sutter, C.; Romero, T.; Janowska, I. Polyvinyl Alcohol-Few Layer Graphene Composite Films Prepared from Aqueous Colloids. Investigations of Mechanical, Conductive and Gas Barrier Properties. Nanomaterials 2020, 10 (5). DOI: 10.3390/nano10050858.
  • Falcone, E.; Sour, A.; Lebrun, V.; Ulrich, G.; Raibaut, L.; Faller, P. Reversible turn-on fluorescent Cu(ii) sensors: rather dream than reality? Dalton Transactions 2019, 48 (38), 14233-14237. DOI: 10.1039/c9dt02864a.
  • Mohanty, A.; Janowska, I. Tuning the structure of in-situ synthesized few layer graphene/carbon composites into nanoporous vertically aligned graphene electrodes with high volumetric capacitance. Electrochimica Acta 2019, 308, 206-216. DOI: 10.1016/j.electacta.2019.04.016.
  • Piantanida, E.; Alonci, G.; Bertucci, A.; De Cola, L. Design of Nanocomposite Injectable Hydrogels for Minimally Invasive Surgery. Accounts of Chemical Research 2019, 52 (8), 2101-2112. DOI: 10.1021/acs.accounts.9b00114.
  • Romiti, F.; del Pozo, J.; Paioti, P. H. S.; Gonsales, S. A.; Li, X. H.; Hartrampf, F. W. W.; Hoveyda, A. H. Different Strategies for Designing Dual-Catalytic Enantioselective Processes: From Fully Cooperative to Non-cooperative Systems. Journal of the American Chemical Society 2019, 141 (45), 17952-17961. DOI: 10.1021/jacs.9b05464.