HAL Id: hal-03006418 https://hal.archives-ouvertes.fr/hal-03006418 Submitted on 16 Nov 2020 HAL is a multi-disciplinary open access archive for the deposit and dissemination of sci- entific research documents, whether they are pub- lished or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L’archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d’enseignement et de recherche français ou étrangers, des laboratoires publics ou privés. A Career in Catalysis: Odile Eisenstein David Balcells, Eric Clot, Stuart Macgregor, Feliu Maseras, Lionel Perrin To cite this version: David Balcells, Eric Clot, Stuart Macgregor, Feliu Maseras, Lionel Perrin. A Career in Catalysis: Odile Eisenstein. ACS Catalysis, American Chemical Society, 2019, 9 (11), pp.10375-10388. 10.1021/ac- scatal.9b02498. hal-03006418
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HAL Id: hal-03006418https://hal.archives-ouvertes.fr/hal-03006418
Submitted on 16 Nov 2020
HAL is a multi-disciplinary open accessarchive for the deposit and dissemination of sci-entific research documents, whether they are pub-lished or not. The documents may come fromteaching and research institutions in France orabroad, or from public or private research centers.
L’archive ouverte pluridisciplinaire HAL, estdestinée au dépôt et à la diffusion de documentsscientifiques de niveau recherche, publiés ou non,émanant des établissements d’enseignement et derecherche français ou étrangers, des laboratoirespublics ou privés.
A Career in Catalysis: Odile EisensteinDavid Balcells, Eric Clot, Stuart Macgregor, Feliu Maseras, Lionel Perrin
To cite this version:David Balcells, Eric Clot, Stuart Macgregor, Feliu Maseras, Lionel Perrin. A Career in Catalysis: OdileEisenstein. ACS Catalysis, American Chemical Society, 2019, 9 (11), pp.10375-10388. �10.1021/ac-scatal.9b02498�. �hal-03006418�
David Balcells,† Eric Clot,‡ Stuart A. Macgregor,§ Feliu Maseras||,* Lionel Perrin¶
† Hylleraas Centre for Quantum Molecular Sciences, Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, Oslo 0315, Norway
‡ IGCM, Univ. Montpellier, CNRS, ENSCM, Montpellier, France
§ Institute of Chemical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, United Kingdom
|| Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avgda. Països Catalans, 16, 43007 Tarragona, Catalonia, Spain.
¶ Université de Lyon, Université Claude Bernard Lyon 1, CPE Lyon, INSA Lyon, ICBMS, CNRS UMR 5246, Equipe ITEMM, Bât Lederer, 1 rue V. Grignard, 69622 Villeurbanne, France
ABSTRACT: On the occasion of Professor Odile Eisenstein’s 70th birthday and her stepping
down as Associate Editor of ACS Catalysis, we reflect on and highlight her distinguished career
in computational chemistry and homogeneous catalysis. In this Account we present selected
examples of her early work on the computational understanding of transition metal complexes,
the evolution of the field towards the quantitative reproduction of these systems, with a final
focus on her specific contributions to important catalytic processes including olefin metathesis,
The authors declare no competing financial interest.
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TOC Graphic
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the First Examples of Isolable Molecular Hydrogen Complexes, M(CO)3(PR3)2(H2) (M = Mo or W; R = Cy or iPr). Evidence for a Side-on Bonded Dihydrogen ligand. J. Am. Chem. Soc. 1984, 106, 451–452.
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theoretical study of an unusual structure. New J. Chem. 1998, 22, 5–9. 17 Gusev, D. G.; Kuhlman, R.; Rambo, J. R.; Berke, H.; Eisenstein, O.; Caulton, K. G. Structural and
Dynamic Properties of OsH2X2L2 (X= Cl, Br, I; L= PiPr3) Complexes: Interconversion between Remarkable Non-Octahedral Isomers. J. Am. Chem. Soc. 1995, 117, 281–292.
18 Maseras, F.; Morokuma, K. A New “Ab Initio + Molecular Mechanics” Geometry Optimization
Scheme of Equilibrium Structures and Transition States. J. Comput. Chem. 1995, 16, 1170–1179. 19 Ujaque, G.; Maseras, F.; Eisenstein, O. Different van der Waals Radii for Organic and Inorganic
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H. Breaking an Electronically Preferred Symmetry by Steric Effects in a Series of [Ir(biph)X(QR3)2] Compounds (X= Cl or I, Q= P or As). New J. Chem. 1998, 22, 1493–1498.
21 Ogasawara, M.; Macgregor, S. A.; Streib, W. E.; Folting, K.; Eisenstein, O.; Caulton, K. G.
Characterization and Reactivity of an Unprecedented Unsaturated Zero-Valent Ruthenium Species: Isolable, Yet Highly Rective. J. Am. Chem. Soc. 1996, 118, 10189–10199.
22 Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. [Ru(Ph)(CO)(PtBu2Me)2]+: A Unique 14-
Electron RuII Complex with Two Agostic Interactions. Angew. Chem. Int. Ed. 1997, 36, 2004–2006.
23 Gottschalk-Gaudig, T.; Huffman, J. C.; Caulton, K. G.; Gérard, H.; Eisenstein, O. Solution and
Solid-State Structure of Ru(CO)2(tBu2PC2H4PtBu2): Square Planar and Monomeric? J. Am. Chem. Soc. 1999, 121, 3242-3243.
24 Ujaque, G.; Cooper, A. C.; Maseras, F.; Eisenstein, O.; Caulton, K. G. Computational Evidence of
the Importance of Substituent Bulk on Agostic Interactions in Ir(H)2(PtBu2Ph)2+. J. Am. Chem. Soc. 1998, 120, 361–-365.
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25 Cooper, A. C.; Clot, E.; Huffman, J. C.; Streib, W. E.; Maseras, F.; Eisenstein, O.; Caulton, K. G.
Computational and Experimental Test of Steric Influence on Agostic Interactions: A Homologous Series for Ir(III). J. Am. Chem. Soc. 1999, 121, 97–106.
26 Ogasawara, M.; Maseras, F.; Gallego-Planas, N.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Unexpecte Coexistence of Isomeric Forms and Unusual Structures of Ru(CO)2L3. Inorg. Chem. 1996, 35, 7468–7469.
27 Ogasawara, M.; Maseras, F.; Gallego-Planas, N.; Kawamura, K.; Ito, K.; Toyota, K.; Streib, W. E.;
Komiya, S.; Eisenstein, O.; Caulton, K. G. Competition between Steric and Electronic Control of Structure in Ru(CO)2L2L’ Complexes. Organometallics 1997, 16, 1979–1993.
28 Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A.;
Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. An h4-Benzene Species Mediates Acetylene Cyclotrimerization. J. Am. Chem. Soc. 1991, 113, 5127–5129.
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30 Bosque, R.; Clot, E.; Fantacci, S.; Maseras, F.; Eisenstein, O.; Perutz, R. N.; Renkema, K. B.;
Caulton, K. G. Inertness of the Aryl-F Bond toward Oxidative Addition to Osmium and Rhodium Complexes: Thermodynamic or Kinetic Origin? J. Am. Chem. Soc. 1998, 120, 12634–12640.
31 Clot, E.; Eisenstein, O.; Naseralla, J.; Macgregor, S. A.; Mcgrady, J. E.; Perutz, R. N. C-F and C-H
Bond Activation of Fluorobenzes and Fluoropyridines at Transition Metal Centers: How Fluorine Tips the Scales. Acc. Chem. Res. 2011, 44, 333–348.
32 Eisenstein, O.; Milani, J.; Perutz, R. N. Selectivity of C-H Activation and Competition between C-
H and C-F Bond Activation at Fluorocarbons. Chem. Rev. 2017, 117, 8710–87153. 33 Lockwood, M. A.; Fanwick, P. E.; Eisenstein, O.; Rothwell, I. P. Mechanistic Studies of the Facile
Four-Electron Reduction of Azobenzene at a Single Tungsten Metal Center. J. Am. Chem. Soc. 1996, 118, 2762–2763.
34 Maseras, F.; Lockwood, M. A.; Eisenstein, O.; Rothwell, I. P. Four-Electron Reduction of Diazo
Compounds at a Single Tungsten Metal Center: A Theoretical Study of the Mechanism. J. Am. Chem. Soc. 1998, 120, 6598–6602.
35 Maron, L.; Eisenstein, O. Do f Electrons Play a Role in the Lanthanide−Ligand Bonds? A DFT
Study of Ln(NR2)3; R = H, SiH3. J. Phys. Chem. A 2000, 104, 7140–7143. 36 Kefalidis, C. E.; Castro, L.; Perrin, L.; Del Rosal, I.; Maron, L. New Perspectives in
Organolanthanide Chemistry from Redox to Bond Metathesis: Insights from Theory. Chem. Soc. Rev. 2016, 45, 2516–2543.
37 Maron, L.; Eisenstein, O. DFT Study of H−H Activation by Cp2LnH d0 Complexes. J Am Chem
Soc. 2001, 123, 1036–1039.
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38 Maron, L.; Perrin, L.; Eisenstein, O. DFT Study of CH4 Activation by d(0) Cl2LnZ (Z = H, CH3)
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Complexes from a DFT Perspective: Reactions of Cp2LnR (R = CH3, H, SiH3) with SiH4 and CH3-SiH3. New J. Chem. 2007, 31, 549–555.
41 Perrin, L.; Maron, L.; Eisenstein, O.; Tilley, T. D. Bond Activations of PhSiH2 by Cp2SmH: A
Mechanistic Investigation by the DFT method. Organometallics 2009, 28, 3767–3775. 42 Maron, L.; Perrin, L.; Eisenstein, O. CF4 Defluorination by Cp2Ln-H: a DFT Study. Dalton Trans.
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44 Maron, L.; Werkema, E. L.; Perrin, L.; Eisenstein, O.; Andersen, R. A. Hydrogen for fluorine
exchange in C6F6 and C6F5H by monomeric [1,3,4-(Me3C)3C5H2]2CeH: Experimental and computational studies. J. Am. Chem. Soc. 2005, 127, 279–292.
45 Raynaud, C.; Perrin, L.; Maron, L. A DFT Study of Stannane Dehydrocoupling Catalyzed by
Cp2LaH. Organometallics 2006, 25, 3143–3151. 46 Guihaume, J.; Raynaud, C.;, Eisenstein, O.; Perrin, L.; Maron, L.; Don Tilley, T. Facile
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Molecules are Involved in the Hydrogenation of Pyridine to Piperidine as Shown by Experiments and Calculations. Inorg. Chem. 2014, 53, 6361–6373.
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49 Toreki, R.; Vaughan, G. A.; Schrock, R. R.; Davis, W. M. Metathetical Reactions of Re(VII)
Alkylidene-Alkylidyne Complexes of the Type Re(CR’)(CHR’)[OCMe(CF3)2]2 (R’ = CMe3 or CMe2Ph) with Terminal and Internal Olefins. J. Am. Chem. Soc. 1993, 115, 127–137.
50 Solans-Monfort, X.; Clot, E.; Copéret, C.; Eisenstein, O. Understanding Structural and Dynamic
Properties of Well-Defined Rhenium-Based Olefin Metathesis Catalysts, Re(≡CR)(=CHR)(X)(Y) from DFT and QM/MM Calculations. Organometallics 2005, 24, 1586–1597.
Metathesis-Catalysts: Which Metal, Which Ligand? J. Am. Chem. Soc. 2007, 129, 8207–8216. 53 Sattely, E. S.; Meek, S.J.; Malcolmson, S.J.; Schrock, R. R.; Hoveyda, A. H. Design and
Stereoselective Preparation of a New Class of Chiral Olefin Metathesis Catalysts and Applications to Enantioselective Synthesis of Quebrachamine: Catalyst Development Inspired by Natural Product Synthesis. J. Am. Chem. Soc. 2009, 131, 943–953.
Monfort, X.; Clot, E.; Eisenstein, O.; Böhm, V. P. W.; Röper, M. b-H Transfer from the Metallacyclobutane: A Key Step in the Deactivation and Byproduct Formation for the Well-Defined Silica-Supported Rhenium Alkylidene Alkene Metathesis Catalyst. J. Am. Chem. Soc. 2008, 130, 6288–6297.
55 Solans-Monfort, X.; Copéret, C.; Eisenstein, O. Shutting Down Secondary Reaction Pathways :
The Essential Role of the Pyrrolyl Ligand in Improving Silica Supported d0-ML4 Alkene Metathesis Catalysts from DFT Calculations. J. Am. Chem. Soc. 2010, 132, 7750–7757.
56 Gordon, C. P.; Yamamoto, K.; Liao, W. C.; Allouche, F.; Andersen, R. A.; Copéret, C.; Raynaud,
C.; Eisenstein, O. Metathesis Activity Encoded in the Metallacyclobutane Carbon-13 NMR Chemical Shift Tensors. ACS Central Sci. 2017, 3, 759-768.
57 Balcells, D.; Raynaud, C.; Crabtree, R. H.; Eisenstein, O. The Rebound Mechanism in Catalytic C-
H Oxidation by MnO(tpp)(Cl) from DFT Studies: Electronic Nature of the Active Species. Chem. Commun. 2008, 744–746.
58 Meunier, B. Metalloporphyrins as Versatile Catalysts for Oxidation Reactions and Oxidative DNA
Cleavage. Chem. Rev. 1992, 92, 1411–1456. 59 Huang, X.; Groves, J. T. Oxygen Activation and Radical Transformations in Heme Proteins and
Metalloporphyrins. Chem. Rev. 2018, 118, 2491–2553. 60 Shaik, S.; Hirao, H.; Kumar, D. Reactivity of High-Valent Iron–Oxo Species in Enzymes and
Synthetic Reagents: A Tale of Many States. Acc. Chem. Res. 2007, 40, 532–542. 61 Jin, N.; Ibrahim, M-; Spiro, T. G.; Groves, J. T. Trans-dioxo Manganese(V) Porphyrins. J. Am.
Chem. Soc. 2007, 129, 12416–12417. 62 Balcells, D.; Raynaud, C.; Crabtree, R. H.; Eisenstein, O. A Rational Basis for the Axial Ligand
Effect in C-H Oxidation by [MnO(porphyrin)(X)]+ (X = H2O, OH-, O2-) from a DFT Study. Inorg.
Chem. 2008, 47, 10090–10099.
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63 Bernadou, J.; Fabiano, A.-S.; Robert, A.; Meunier, B. "Redox Tautomerism" in High-Valent Metal-
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O. Manganese Catalysts for C-H Activation: An Experimental/Theoretical Study Identifies the Stereoelectronic Factor that Controls the Switch between Hydroxylation and DesaturationPpathways. J. Am. Chem. Soc. 2010, 132, 7605–7616.
68 Das, S.; Incarvito, C. D.; Crabtree, R. H.; Brudvig, G. W. Molecular Recognition in the Selective
Oxygenation of Saturated C-H Bonds by a Dimanganese Catalyst. Science 2006, 312, 1941–1943.
69 Balcells, D.; Moles, P.; Blakemore, J. D.; Raynaud, C.; Brudvig, G. W.; Crabtree, R. H.; Eisenstein, O. Molecular Recognition in Mn-catalyzed C-H Oxidation. Reaction Mechanism and Origin of Selectivity from a DFT Perspective. Dalton Trans. 2009, 5989–6000.
70 Blakemore, J. D.; Crabtree, R. H.; Brudvig, G. W. Molecular Catalysts for Water Oxidation. Chem.
Rev. 2015, 115, 12974–13005. 71 Hull, J. F.; Balcells, D.; Blakemore, J. D.; Incarvito, C. D.; Eisenstein, O.; Brudvig, G. W.;
Crabtree, R. H. Highly Active and Robust Cp* Iridium Complexes for Catalytic Water Oxidation. J. Am. Chem. Soc. 2009, 131, 8730–8731.
72 Blakemore, J. D.; Schley, N. D.; Balcells, D.; Hull, J. F.; Olack, G. W.; Incarvito, C. D.; Eisenstein,
O.; Brudvig, G. W.; Crabtree, R. H. Half-sandwich Iridium Complexes for Homogeneous Water-Oxidation Catalysis. J. Am. Chem. Soc. 2010, 132, 16017–16029.
73 Hintermair, U.; Sheehan, S. W.; Parent, A. R.; Ess, D. H:; Richens, D. T.; Vaccaro, P. H.; Brudvig,
G. W.; Crabtree, R. H. Precursor Transformation during Molecular Oxidation Catalysis with Organometallic Iridium Complexes. J. Am. Chem. Soc. 2013, 135, 10837–10851.
74 Ingram, A. J.; Wolk, A. B.; Flender, C.; Zhang, J.; Johnson, C. J.; Hintermair, U.; Crabtree, R. H.;
Johnson, M. A.; Zare, R. N. Modes of Activation of Organometallic Iridium Complexes for Catalytic Water and C–H Oxidation. Inorg. Chem. 2014, 53, 423–433.