Synthesis and electrochemical reduction of a ruthenium complex bearing an N,N-Bis[(benzo[g][1,5]naphthyridin-2-yl)methyl]propane-2-amine ligand as an NAD+/NADH-type redox site

Angewandte Chemie - International Edition

Volumn 47, Issue 50, 2008, Pages 9768-9771

  Kimura, Masahiro ^a   Tanaka, Koji ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

Electrochemistry; N ligands; Redox chemistry; Reduction; Ruthenium

Indexed keywords

AMINES; CARBON MONOXIDE; CHELATION; CHEMICAL REACTIONS; ELECTROCHEMISTRY; ELECTROLYTIC REDUCTION; LIGANDS; ORGANIC COMPOUNDS; PROPANE; RUTHENIUM; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINE LIGANDS; BIPYRIDINE; CHEMICAL EQUATIONS; ELECTROCHEMICAL REDUCTIONS; ELECTRON REDUCTIONS; N LIGANDS; PIVALIC ACIDS; REDOX CHEMISTRY; REDOX SITES; RUTHENIUM COMPLEXES;

REDUCTION;

LIGAND; NICOTINAMIDE ADENINE DINUCLEOTIDE; ORGANOMETALLIC COMPOUND; RUTHENIUM;

ARTICLE; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION;

HYDROGENATION; LIGANDS; NAD; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RUTHENIUM;

EID: 57049109828     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804404     Document Type: Article

References (27)

1. For recent reviews of hydrogenation, see: Acc. Chem. Res. 2007, 40 (12), special issue;
2. a) M. Ito, T. Ikariya, Chem. Commun. 2007, 5134;
3. b) N. K. Szymczak, D. R. Tyler, Coord. Chem. Rev. 2008, 252, 212.
4. a) C. Walsh, Acc. Chem. Res. 1980, 13, 148, and references therein;
5. b) D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223.
6. For recent articles of transfer hydrogenation with NADH model, see: a) K. Akagawa, H. Akabane, S. Sakamoto, K. Kudo, Org. Lett. 2008, 10, 2035;
7. b) Q. Kang, Z.-A. Zhao, S.-L. You, Org. Lett. 2008, 10, 2031;
8. c) J. Canivet, G. Süss-Fink, P. Štěpnička, Eur. J. Inorg. Chem. 2007, 4736;
9. d) N. J. A. Martin, L. Ozores, B. List, J. Am. Chem. Soc. 2007, 129, 8976;
10. e) J. W. Yang, B. List, Org. Lett. 2006, 8, 5653;
11. f) N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368;
12. g) J. B. Tuttle, S. G. Ouellet, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 12662;
13. h) F. Hollmann, A. Kleeb, K. Otto, A. Schmid, Tetrahedron: Asymmetry 2005, 16, 3512;
14. i) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781.
15. For catalytic use of NADH model compound, see: j) H. J. Xu, Y. C. Liu, Y. Fu, Y. D. Wu, Org. Lett. 2006, 8, 3449.
16. T. Koizumi, K. Tanaka, Angew. Chem. 2005, 117, 6041;
17. Angew. Chem. Int. Ed. 2005, 44, 5891.
18. a) A. Godard, G. Quguiner, J. Heterocycl. Chem. 1980, 17, 465;
19. b) H. Tannai, T. Koizumi, K. Tanaka, Inorg. Chim. Acta 2007, 360, 3075.
20. a) H. Tannai, T. Koizumi, T. Wada, K. Tanaka, Angew. Chem. 2007, 119, 7242;
21. Angew. Chem. Int. Ed. 2007, 46, 7112;
22. b) D. Polyansky, D. Cabelli, J. T. Muckerman, E. Fujita, T. Koizumi, T. Fukushima, T. Wada, K. Tanaka, Angew. Chem. 2007, 119, 4247;
23. Angew. Chem. Int. Ed. 2007, 46, 4169.
24. 2+ (m/z = 364.2) became the major signal.
25. 2+.
26. 2 consumed more than five molar equivalents of electricity. Attempts to identify the reduction product were not successful as a result of the extreme lability of the product.
27. A. Bondi, J. Phys. Chem. 1964, 68, 441.