Electron and proton reservoir complexes: Thermodynamic basis for C-H activation and applications in redox and dendrimer chemistry

Accounts of Chemical Research

Volumn 33, Issue 5, 2000, Pages 287-298

  Astruc, Didier ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; HETEROCYCLIC COMPOUND; IRON; OXIDIZING AGENT; POLYAMINE; POLYCYCLIC HYDROCARBON; PROTON; REDUCING AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPLEX FORMATION; ELECTRON; ELECTRON TRANSPORT; OXIDATION; OXIDATION REDUCTION REACTION; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

EID: 0034114611     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9901319     Document Type: Article

References (65)

1. Lehn, J.-M. Supramolecular Chemistry. Concepts and Perspectives; VCH: Weinheim, 1995.
2. Balzani, V.; Scandola, F. Supramolecular Chemistry; Ellis Hordwood: New York, 1991.
3. Bertini, I.; Gray, H. B. Lippard, S. J. Valentine, J. S. Bioinorganic Chemistry; University Science Books: Mill Valley, CA, 1994.
4. Taube, H. Electron-Transfer of Complex Ions in Solutions; Academic Press: New York, 1970.
5. Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic Press: New York, 1978.
6. Marcus, R. A.; Sutin, N. Electron Tranfers in Chemistry and Biology. Biochim. Biophys. Acta 1985, 811, 265-322.
7. Paramagnetic Species in Activation, Selectivity and Catalysis; Chanon, M., Juliard, M., Poite, J. C., Eds.; Kluwer: Dordrecht, 1988.
8. Electron and Proton Transfer in Chemistry and Biology; Müller, A., Ratajczak, H., Junge, W., Diemann, E., Eds.; Elsevier: Amsterdam, 1992.
9. Astruc, D. Electron Transfer and Radical Processes in Transition Metal Chemistry; VCH: New York, 1995.
10. 6, a Key Class Active in Redox Catalysis. J. Am. Chem. Soc. 1979, 101, 5445-5447.
11. Astruc, D. Organoiron Electron Reservoir Complexes. Acc. Chem. Res. 1986, 19, 377-383.
12. 2+ (R = H or Me), a Novel Family of Strong Oxidants: Isolation, Characterization, Electronic Structure, and Redox Properties. J. Am. Chem. Soc. 1998, 120, 11693-11705.
13. n+ (n = 1,0). J. Chem. Soc., Chem. Commun. 1982, 1383-1384.
14. 4. J. Am. Chem. Soc. 1982, 704, 3755-3757.
15. 2: Bifunctionalization via Protection by Hydride. Organometallics 1990, 9, 341-346.
16. 4-Polyene)]. Organometallics 1990, 9, 2155-2164.
17. 6-Benzene) Iron (0) Derivatives. Nouv. J. Chim. 1985, 9, 41-50.
18. + from Exo-Substituted Cyclohexadiene Fe(0) Complexes: A Key in the Synthesis of Heterobifunctional Cyclohexadienes from Benzene. J. Am. Chem. Soc. 1986, 108, 1320-1321.
19. Mandon, D.; Astruc, D. Nucleoplilic Attack on the Cyclohexadienyl Ligand: From Mono to Heterobifunctional Cyclohexadiene Iron Complexes and the Role of the Electron-Transfer Pathway in Hydride Abstraction. Organometallics 1989, 8, 2372-2377.
20. 1Cp(arene)]. J. Am. Chem. Soc. 1997, 119, 11132-11133.
21. n, x = 0-IV, R = H or Me; n = -1 to + 3. J. Am. Chem. Soc. 1999, 121, 5674-5686.
22. Parker, V.; Handoo, K. L.; Roness, F.; Tilset, M. Electrode Potentials and the Thermodynamics of Isodesmic Reactions. J. Am. Chem. Soc. 1991, 113, 7493.
23. Moore, E. J.; Sullivan, J. M.; Norton, J. R. Kinetics and Thermodynamic Acidity of Hydrido Transition-Metal Carbonyl Complexes. J. Am. Chem. Soc. 1986, 108, 2257-2263.
24. Tilset, M.; Parker, V. D. Solution Homolytic Bond Dissociation Energies of Organotransition-Metal Hydrides. J. Am. Chem. Soc. 1989, 111, 6711.
25. Protasiewicz, J. D.; Theopold, K. H. A Direct Comparison of the Rates of Degenerate Transfer of Electrons, Protons, Hydrogen Atoms between Metal Complexes. J. Am. Chem. Soc. 1993, 115, 5559.
26. 2SO Mixtures: A Kinetic, NMR, and EHMO Study. Organometallics 1994, 13, 690-697.
27. Zhang, X.-M.; Bordwell, F. G. Effects of π-Coordinated Transition-Metal Groups on Fluorene Acidities and Homolytic Bond Dissociation Enthalpies. Organometallics 1994, 13, 2920.
28. a of Triphenylcyclopropene. Electrochemical Determination of an Inaccessible Equilibrium Constant. J. Am. Chem. Soc. 1969, 91, 5182.
29. Wayner, D. D. M.; Parker, V. D. Bond Energies in Solution from Electrode Potentials and Thermodynamic Cycles. A Simplified and General Approach. Acc. Chem. Res. 1993, 26, 287-294.
30. Tilset, M. One-Electron Oxidation of Cyclopentadienylchromium Carbonyl Hydrides: Thermodynamics of Oxidative Addition of Metal-Hydrogen Bonds toward Homolytic and Heterolytic Cleavage. J. Am. Chem. Soc. 1992, 114, 2740.
31. Tilset, M.; Hamon, J.-R.; Hamon, P. Relative Bond M-X Bond Dissociation Energies in 16, 17 and 18e Organo-Transition Metal Complexes (X = Halide, H). Chem. Commun. 1998, 765-766.
32. 6)]. J. Chem. Soc., Chem. Commun. 1993, 333-334.
33. 1Cp(arene)] Sandwiches as Efficient and Selective Electrocatalysts: Syntheses of Homo- and Heterodi-nuclear Zwitterionic Transition-Metal Fulvalene Complexes. Organometallics 1996, 15, 2360-2372.
34. Alonso, E.; Ruiz, J.; Astruc, D. The Use of the Electron-Reservoir Complexes [Fe(I)Cp(arene)] for the Electrocatalytic Synthesis of Redox-Reversible Metal-Carbonyl Clusters Containing Ferrocenyldiphenylphosphine. J. Cluster Sci. 1998, 9, 271-287.
35. Valério, C.; Fillaut, J.-L.; Ruiz, J.; Guittard, J.; Blais, J.-C.; Astruc, D. The Dendritic Effect in Molecular Recognition: Ferrocene Dendrimers and their Use as Supramolecular Redox Sensors for the Recognition of Small Inorganic Anions. J. Am. Chem. Soc. 1997, 119, 2588-2589.
36. + Termini which Recognizes Chloride and Bromide Anions. Angew. Chem., Int. Ed. Engl. 1999, 38, 1747-1751.
37. Ruiz, J.; Astruc, D. Permethylated Electron-Reservoir Sandwich Complexes as References for the Determination of Redox Potentials. Suggestion of a New Redox Scale. C. R. Acad. Sci. Paris, t. 1, Sér. II c 1998, 21-27.
38. Moulines, F.; Astruc, D. Tentacled Iron Sandwichs. Angew. Chem., Int. Ed. Engl. 1988, 27, 1347-1349.
39. Fillaut, J.-L.; Astruc, D. Tentacled Aromatics: from Central-Ring to Outer-Ring Iron Sandwich Complexes. J. Chem. Soc., Chem. Commun. 1993, 1320-1322.
40. -. Synlett 1992, 55-56.
41. Fillaut, J.-L.; Linares, J.; Astruc, D. Single-Step Six-Electron Transfer in a Heptanuclear Complex: Isolation of Both Redox Forms. Angew. Chem., Int. Ed. Engl. 1994, 33. 2460-2462.
42. + Complexes and Polyfunctionalization of the Tentacles with Iron Sandwich Redox Centers. New J. Chem. 1996, 20, 945 957.
43. Moulines, F.; Djakovitch, L.; Fillaut, J.-L.; Astruc, D. Hexahydrozirconation versus Hexahydroboration Routes to Hexaiodo Tentacled Aromatic Iron Sandwichs. Synlett 1992, 57-58.
44. Marvaud, V.; Astruc, D.; Leize, E.; Van Dorsselaer, A.; Guittard, J.; Blais, J.-C. Synthesis and Mass Spectral Characterization of Iron-Centered Hexa-Polypyridine Stars and Their Hexa-Ruthenium Complexes. New J. Chem. 1997, 21, 1309-1319.
45. 60 End-Capped Polystyrene Stars. J. Chem. Soc., Chem. Commun. 1996, 1565-1566.
46. Moulines, F.; Gloaguen, B.; Astruc, D.One-Pot Multifunctionalization of Polymethyl Hydrocarbon π-Ligands. Maximum space Occupancy by Double Branching and Formation of Arborols. Angew. Chem., Int. Ed. Engl. 1992, 28, 458-460.
47. Siegel, J.; Gutiérrez, A.; Scheizer, W. B.; Ermer, O.; Mislow, K. Static and Dynamic Stereochemistry of Hexaisopropylbenzene. J. Am. Chem. Soc. 1986, 108, 1569-1575.
48. Gloaguen, B.; Astruc, D. Chiral Pentaisopropyl- and Pentaisopentyl Complexes: One-Pot Synthesis by Formation of Ten Carbon-Carbon Bonds from Pentamethylcobaticinium. J. Am. Chem. Soc. 1990, 112, 4607-4609.
49. Buchholz, D.; Gloaguen, B.; Fillaut, J.-L.; Cotrait, M.; Astruc, D. Mono- and Bis(pentaisopropylcyclopentadienyl) Cobalt and Rhodium Sandwich Complexes and Other Decabranched Cyclopentadienyl Complexes. Chem. Eur. J. 1995, 1, 374-381.
50. Tomalia, D. A.; Naylor, A. N.; Goddard, W. A., III Starburst Dendrimers: Molecular-Level Control of Size, Shape, Surface Chemistry, Topology and Flexibility in the Conversion of Atoms to Macroscopic Materials. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
51. Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Syntheses and Perspectives; VCH: New York, 1996.
52. 6]. Angew. Chem., Int. Ed. Engl. 1994, 33, 1637-1639.
53. 6]. C. R. Acad. Sci. Paris, t. 2, Sér. II c 1999, 205-208.
54. Newkome, G. R.; He, E.; Moorefield, C. N. Suprasupermolecules with Novel Properties: Metallodendrimers. Chem. Rev. 1999, 99, 1689-1746.
55. Casado, C. M.; Cuadrado, I.; Morán, M.; Alonso, B.; Garcia, B.; Gonzalès, B.; Losada, J. Redox-Active Ferrocenyl Dendrimers and Polymers in Solution and Immobilized on Electrode Surfaces. Coord. Chem. Rev. 1999, 185-186, 53-79.
56. Majoral, J.-P.; Caminade, A.-M. Dendrimers Containing Heteroatoms (Si, P, B, Ge or Bi). Chem. Rev. 1999, 99, 845-880.
57. Hearshaw, M. A.; Moss, J. R. Organometallic and Related Metal-Containing Dendrimers. Chem. Commun. 1999, 1-8.
58. + Induced Nona-Allylation of Mesitylene and Phase-Transfer Catalyzed Synthesis of a Redox-Active Nonairon Complex. Angew. Chem., Int. Ed. Engl. 1993, 32, 1075-1077.
59. + termini. New J. Chem. 1997, 21, 1139-1141.
60. Valério, C.; Ruiz, J.; Fillaut, J.-L.; Astruc, D. Dendritic Effect in the Recognition of Small Inorganic Anions Using a Polycationic Nona-Cobalticinium Dendrimer. C. R. Acad. Sci. Paris, t. 2, Sér. II c 1999, 79-83.
61. Sartor, V.; Djakovitch, L.; Fillaut, J.-L.; Moulines, F.; Neveu, F.; Marvaud, V.; Guittard, J.; Blais, J.-C.; Astruc, D. Organoiron Route to a New Dendron for Fast Dendritic Syntheses using Divergent and Convergent Methods. J. Am. Chem. Soc. 1999, 121, 2929-2930.
62. Bosman, A. W.; Janssen, H. M.; Meijers, E. W. About Dendrimers: Structure, Physical Properties, and Applications. Chem. Rev. 1999, 99, 1665-1688.
63. Beer, P. D. Transition-Metal Receptor Systems for the Selective Recognition of Anion Sensing of Anionic Guest Species. Acc. Chem. Res. 1998, 31, 71-80.
64. Ewing, A. G.; Strein, T. G.; Lau, Y. Y. Analytical Chemistry in Microenvironments: Single Nerve Cells. Acc. Chem. Res. 1992, 25, 440-447.
65. Xia, Y.; Rogers, J. A.; Paul, K. E.; Whitesides, G. M. Unconventional Methods for Fabricating and Patterning Nanostructures. Chem. Rev. 1999, 99, 1823-1848.