Chemistry towards life sciences

+33 1 76 53 43 07, room T216-7

Laboratoire de Chimie et Biochimie pharmacologiques et toxicologiques (LCBPT) – CNRS UMR 8601
Université Paris Descartes
45 Rue des Saints Pères
75270 Paris Cedex 06
France

Curriculum Vitae

Academic and Professional Background :

AWARDS:

Fundings:

2019	ANR JCJC (PhotoChiraPhane)
2019	IdEx “Dynamique Recherche” Université Paris Cité (projet pCpPhotoCat)

Scientific interests:

Development of innovative methods to prepare and selectively functionalize planar chiral [2.2]paracyclophane derivatives. Synthesis and characterization of three-dimensional luminophores and RNA ligands based on the [2.2]paracyclophane scaffold.

Publications

1. Wu, S.; Micouin L.; Benedetti E. “Practical access to planar chiral benzophenones derived from [2.2]paracyclophane” Synlett 2024, Accepted Manuscript, DOI: 10.1055/a-2284-4984.
   
2. Flichot, H.; Sickinger, A.; Brom, J.; Lefeuvre, B.; Dorcet, V.; Guizouarn, T.; Cador, O.; Le Guennic, B.; Micouin, L.; Maury, O.; Benedetti, E.; Pointillart, F. “Magneto-structural correlation in lanthanide luminescent [2.2]Paracyclophane-based Single-Molecule Magnets“  Dalton Trans. 2024, Accepted Manuscript, DOI:10.1039/D4DT00536H.
3. Wu, S.; Felder, S.; Brom, J.; Pointillart, F.; Maury, O.; Micouin L.; Benedetti E. [2.2]Paracyclophanes: from selective functionalization to optical properties Adv. Optical. Mater. 2024, Accepted Manuscript
4. Benedetti, E.; Delcourt, M.-L.; Felder, S.; Wu, S.; Brom, J.; Micouin, L. [2.2]Paracyclophanes: exploring new dimensions Actu. Chimique, 2024, 451, 18.
5. Benedetti, E.; Micouin, L. Have spirocyclic scaffolds been properly utilized in recent drug discovery efforts? Expert Opin. Drug Discov. 2024, Just accepted. DOI: 10.1080/17460441.2024.2305735
6. Brom, J.; Maruani, A.; Turcaud, S.; Lajnef, S.; Peyrot, F.; Micouin, L.; Benedetti, E. “[2.2]Paracyclophane-based coumarins: effective organo-photocatalysts for light-induced desulfonylation processes” Org. Biomol. Chem. 2024, 22, 59-64. DOI: 10.1039/D3OB01711G(Preprint ChemRxiv – DOI: 10.26434/chemrxiv-2023-n4ds3).
7. Brom, J.; Maruani, A.; Micouin, L.; Benedetti, E. “Light-driven reductive cleavage of sulfonamides promoted by thiourea organophotosensitizers”. J. Org. Chem. 2023,  88, 5923. DOI: 10.1021/acs.joc.3c00296 (Preprint ChemRxiv – DOI: 10.26434/chemrxiv-2022-jvdqw)
8. Fleurisson, C.; Graidia, N.; Foricher, Y.; Benedetti, E.; Micouin, L.;  “Intramolecular Buchwald-Hartwig N-Arylation of Bicyclic Hydrazines: Practical Access to Spiro[indoline-2,3′-piperidines]”  Org. Biomol. Chem. 2023, 21, 3542. DOI: 10.1039/D3OB00406F (Preprint ChemRxiv – DOI: 10.26434/chemrxiv-2022-rqsqc)
9. Felder, S.; Delcourt, M.-L.; Rodríguez, R.; Favereau, L.; Jeanne Crassous, J.; Micouin, L.; Benedetti, E. “Compact CPL emitters based on a [2.2]paracyclophane scaffold: recent developments and future perspectives”, J. Mater. Chem. C 2023, 11, 2053 DOI: https://doi.org/10.1039/D2TC04885J
10. S. Felder, C. Sagné, E. Benedetti, L. Micouin “Small-Molecule 3D Ligand for RNA Recognition: Tuning Selectivity through Scaffold Hopping” ACS Chemical Biology, 2022, 17, 3069. DOI: https://doi.org/10.1021/acschembio.2c00171
11. S. Felder, M.-L. Delcourt, M.H.E. Bousquet, D.  Jacquemin, R. Rodríguez, L. Favereau, J. Crassous, L. Micouin, E. Benedetti “Planar chiral analogues of PRODAN based on a [2.2]paracyclophane scaffold: Synthesis and photophysical studies”. J. Org. Chem. 2022, 87, 147-158 DOI: https://doi.org/10.1021/acs.joc.1c02071
12. S. Wu, L.A. Galan, M. Roux, F. Riobe, B. Le Guennic, Y. Guyot, T. Le Bahers, L. Micouin, O. Maury, E. Benedetti “Tuning the excited state properties of [2.2]paracyclophane-based antennas to ensure efficient sensitization of lanthanide ions or singlet oxygen generation” Inorg. Chem. 2021, 60, 16194−16203. DOI: https://doi.org/10.1021/acs.inorgchem.1c01986
13. S. Felder, S. Wu, J. Brom, L. Micouin, E. Benedetti,  “Enantiopure planar chiral [2.2]paracyclophanes: Synthesis and applications in asymmetric organocatalysis” Chirality, 2021, 33, 506-527 DOI: https://doi.org/10.1002/chir.23335
14. S. Felder, L. Micouin, E. Benedetti “Para‐functionalization of N‐substituted 4‐amino[2.2]paracyclophanes by regioselective formylation” Eur. J. Org. Chem., 2021, 4015-4018. DOI: https://doi.org/10.1002/ejoc.202100288
15. C. Fleurisson, E. Benedetti, L. Micouin Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications Synlett 2021, 31, 858-874. DOI: 10.1055/s-0040-1707324
16. M.-L.Delcourt, C. Reynaud, S. Turcaud, L. Favereau, J. Crassous, L. Micouin, E. Benedetti, 3D Coumarin Systems Based on [2.2]Paracyclophane: Synthesis, Spectroscopic Characterization, and Chiroptical Properties. J. Org. Chem. 2019, 84 , 888–899. https://doi.org/10.1021/acs.joc.8b02773.
17. M.-L. Delcourt, S. Felder, S. Turcaud, C. H. Pollok, C. Merten, L. Micouin, E. Benedetti,  Highly Enantioselective Asymmetric Transfer Hydrogenation: A Practical and Scalable Method To Efficiently Access Planar Chiral [2.2]Paracyclophanes. J. Org. Chem. 2019, 84 , 5369–5382. https://doi.org/10.1021/acs.joc.9b00372.
18. R. Piccardi, S. Turcaud, E. Benedetti, L. Micouin, Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents. Synthesis, 2019, 51 , 97–106. https://doi.org/10.1055/s-0037-1610392 (Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue)
19. M.-L. Delcourt, S. Simon, E. Benedetti, L.Micouin, Highly Enantioselective Desymmetrization of Centrosymmetric pseudo-para-Diformyl[2.2]paracyclophane via Asymmetric Transfer Hydrogenation ACS Catalysis, 2018, 8, 6612-6616
20. E. Benedetti, M.-L. Delcourt, B. Gatin-Fraudet, S. Turcaud, L.Micouin “Synthesis and photophysical studies of through-space conjugated [2.2]paracyclophane-based naphthalene fluorophores” RSC Advances, 2017, 7, 50472-50476
21. R. Piccardi, A. Coffinet, S. Turcaud, E. Benedetti, L. Micouin, “Continuous flow synthesis of dimethylalkynylaluminum reagents.” Synthesis, 2016, 48, 3272 .
22. N. Duchemin, E. Benedetti, L. Bethge, S. Vonhoff, S. Klussmann, J.-J. Vasseur, J. Cossy, M. Smietana, S. Arseniyadis, “Expanding biohybrid-mediated asymmetric catalysis into the realm of RNA.” Chem. Commun.2016, 52, 8604.
23. K. Amirbekyan, N. Duchemin, E. Benedetti, R. Joseph, A. Colon, S. Markarian, L. Bethge, S. Vonhoff, S. Klussmann, J. Cossy, J.-J. Vasseur, S. ; Arseniyadis, M. Smietana, “Design, Synthesis and Binding Affinity Evaluation of New Hoechst 33258 Derivatives for the Development of Sequence-specific DNA-based Asymmetric Catalysts.”ACS Catal. 2016, 6, 3096.
24. M.-L. Delcourt, S. Turcaud, E. Benedetti, L. Micouin, “Efficient and scalable kinetic resolution of racemic 4 formyl[2.2]paracyclophane via asymmetric transfer hydrogenation.” Adv. Synth. Catal. 2016, 358, 1213.
25. L. Iannazzo, E. Benedetti, M. Catala, M. Etheve-Quelquejeu, C. Tisne, L. Micouin,
     “Monitoring of reversible boronic acid-diol interactions by fluorine NMR spectroscopy in aqueous media.” Org. Biomol. Chem. 2015, 13, 8817.
26. E. Benedetti, N. Duchemin, L. Bethge, S. Vonhoff, S. Klussmann, J.-J. Vasseur, J. Cossy, M. Smietana, S. Arseniyadis, “DNA-cellulose: An economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis.” Chem. Commun. 2015, 51, 6076 (Front Cover, Synfacts2015, 11, 773).
27. R. Barberon, E. Benedetti, J.-J. Vasseur, J. Cossy, S. Arseniyadis, M. Smietana, “Recent Developments in Alkyne Borylations.” Tetrahedron 2014, 70, 843.
28. J. Wang, E. Benedetti, L. Bethge, S. Vonhoff, S. Klussmann, J.-J. Vasseur, J. Cossy, M. Smietana, S. Arseniyadis, “DNA vs. mirror image DNA: A universal approach to tune the absolute configuration in DNA-based asymmetric catalysis” Angew. Chem. Int. Ed. 2013, 52, 1156.
29. E. Benedetti, A.B.E. Veliz M. Charpenay, L. S. Kocsis, K. M. Brummond, “Attachable solvatochromic fluorophores and bioconjugation studies” Org. Lett. 2013, 15, 2578.
30. L. S. Kocsis, E. Benedetti, K. M. Brummond “Microwave-assisted intramolecular dehydrogenative Diels-Alder reactions for the synthesis of functionalized naphthalenes/solvatochromic dyes,” J. Vis. Exp. 2013, 74, e50511 (doi:http://dx.doi.org/10.3791/50511).
31. L. S. Kocsis, E. Benedetti, K. M. Brummond. “A thermal dehydrogenative Diels-Alder reaction of styrenes for the concise synthesis of functionalized naphthalenes” Org. Lett. 2012, 14, 4430 (Synfacts2012, 8, 1199).
32. E. Benedetti, L. S. Kocsis, K. M. Brummond “Synthesis and photophysical properties of a series of cyclopenta[b]naphthalene solvatochromic fluorophores” J. Am. Chem. Soc. 2012, 134, 12418 (Synfacts 2012, 8, 1089).
33.  Kitahara, K. ; Toma, T.; Shimokawa J ; Fukuyama, T ; Checked  by Benedetti, E.; Brummond, K. M. “Efficient Synthesis of Oxime Using O-TBS-N-Tosylhydroxylamine: Preparation of (2Z)-4-(Benzyloxy)but-2-enal Oxime” Org. Synth. 2012, 89, 480-490 DOI: https://doi.org/10.15227/orgsyn.089.0480
34. E. Benedetti, M. Lomazzi, F. Tibiletti, J.-P. Goddard L. Fensterbank, M. Malacria, G. Palmisano, A. Penoni, “Synthesis of nitrogen contaning heterocycles via ring-closing ene-ene and ene-yne metathesis reactions. An easy access to 1- and 2-benzazepine scaffolds and five- and six-membered lactams” Synthesis 2012, 44, 3523.
35. E. Benedetti, A. Simonneau, A. Hours, H. Amouri, A. Penoni, G. Palmisano, M. Malacria, J.-P. Goddard L. Fensterbank, “(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl2]2}: a novel efficient catalyst for the cycloisomerizations of homopropargylic diols and N-tethered enynes” Adv. Synth. Catal. 2011, 353, 1908.
36. E. Benedetti, G. Lemière, L.-L. Chapellet, A. Penoni, G. Palmisano, M. Malacria, J.-P. Goddard, L. Fensterbank, “Gold(I)-catalyzed cyclization of β-allenylhydrazones: an efficient synthesis of multisubtituted N-amino pyrroles” Org. Lett. 2010, 12, 4396.

Book chapters

1. Bicyclic 5-5 systems with one ring junction nitrogen atom: Two extra heteroatoms 2:0 Benedetti, E.; Micouin, L. Reference Collection in Chemistry, Molecular Science and Chemical Engineering Wiley, 2022. Volume 11, pp 145-173. DOI:10.1016/B978-0-12-409547-2.14935-2 
2. Multicomponent reactions in natural product synthesis. Smietana, M.; Benedetti, E.; Bressy, C.; Arseniyadis S. in Efficiency in Natural Products Total Synthesis, (Eds. P.-Q. Huang, Z.-J. Yao, R. P. Hsung), Wiley, 2018 Chapter 8, pp 319-344.
3. Recent applications of kagan’s reagent (SmI₂) in natural product synthesis. Benedetti, E.; Bressy, C.; Smietana, M.; Arseniyadis, S. in Efficiency in Natural Products Total Synthesis, (Eds. P.-Q. Huang, Z.-J. Yao, R. P. Hsung), Wiley, 2018 Chapter 6, pp 273-295.
4. Synthesis of polyketides. Bressy, C.; Smietana, M.; Benedetti, E.; Arseniyadis S. in From Biosynthesis to Total Synthesis, (Ed. A.L. Zografos), Wiley 2016, Chapter 2, pp 44-86.

Patents

1. Functionalized naphthalene fluorophores, Brummond, K. M.; Kocsis, L. S.; Benedetti, E. U.S. Patent No 9,133,234 B2.  Publication date: 15/09/2015.
2. Synthesis, structure and use of functionalized naphthalenes, Brummond, K. M.; Kocsis, L. S.; Benedetti, E. U.S. Patent No 9,102,703 B2. Publication date: 11/08/2015.