Design of bifunctional molecular catalysts for hydrogenation of polar functionalities

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 66, Issue 11, 2008, Pages 1042-1048

  Ito, Masato ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGENATION;

CATALYTIC PERFORMANCE; CHIRAL COMPOUNDS; EFFICIENT CATALYSTS; MOLECULAR CATALYSTS; MOLECULAR HYDROGEN; RECENT PROGRESS; REDUCTIVE TRANSFORMATIONS; STRUCTURAL MODIFICATIONS;

CATALYSTS;

EID: 60249084725     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.66.1042     Document Type: Article

References (42)

1. (a) Ito, M.; Ikariya, T. Chem. Commun. 2007, 5134.
2. nd Edn; Beller, M.; Bolm, C., Eds.; Wiley-VCH, Weinheim, Germany, 2004, vol. 2; pp 29-103.
3. (c) Noyori, R.; Ohkuma, T. Angew. Chem, Int. Ed. Engl. 2001, 40, 40.
4. (a) Ito, M.; Hirakawa, M.; Murata, K.; Ikariya, T. Organometallics 2001, 20, 379.
5. (b) Hedberg, C.; Källström, K.; Arvidsson, P. I.; Brandt, P.; Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083.
6. (c) Paptchikhine, A.; Källström, K.; Andersson, P. G. C. R. Chimie 2007, 10, 213.
7. 2 has recently received support in the following literatures: (a) Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490.
8. (b) Rautenstrauch, V.; Hoang-Cong, X.; Churland, R.; Abdur-Rashid, K.; Morris, R. H. Chem. Eur. J. 2003, 9, 4959.
9. (c) Casey. C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100.
10. 2(diphosphine) (diamine). The following are the leading references on the "Ru/NH bifunctionality" which characterizes this catalytic behavior, (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
11. (b) Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
12. (c) Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
13. (d) Petra, D. G.; Reek, J. N. H.; Handgraaf, J.-W; Meijer, E. J.; Dierkes, P.; Kamer, P. C. J.; Brusse, J.; Shoemaker, H. E.; van Leeuwen, P. W. N. M. Chem. Eur. J. 2000, 6, 2818.
14. (e) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931.
15. (f) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998.
16. (g) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
17. (h) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
18. (a) Ito, M.; Osaku, A.; Kobayashi, C.; Shiibashi, A.; Ikariya, T. to be submitted.
19. (b) Ito, M.; Ashiarai, M.; Ikariya, T. Abstr. Symp. Organomet. Chem. Jpn. 2005, 52, 90.
20. (c) Ito, M.; Ashiarai, M.; Ikariya, T. Annual Meeting of Chem. Soc. Jpn. 2005, 85, 3C426.
21. (d) Ito, M.; Yamaguchi, K.; Ikariya, T. Annual Meeting of Chem. Soc. Jpn. 2007, 87, 3R117.
22. (e) Ito, M.; Yamaguchi, K.; Ashiarai, M.; Ikariya, T. Ahstr. Symp. Coord. Chem. Jpn., 2008, 58, 2Da-18.
23. 2] complex is reported to have an Ru-Cl distance of 2.5116(9) Å, which is slightly shorter than that in 3a. Wang, M. H.; Englert, U.; Koelle, U. J. Organomet. Chem. 1993, 453, 127.
24. (a) Peloso, A.; Dolcetti, G.; Ettore, R. Inorg. Chim. Acta 1967, 1, 403.
25. (b) Marynick, D. S. J. Am. Chem. Soc. 1984, 106, 4064.
26. (c) Darensbourg, M. Y.; Longridge, E. M.; Payne, V.; Reibenspies, J.; Riordan, C. G.; Springs, J. J.; Calabrese, J. C. Inorg. Chem. 1990, 29, 2721.
27. Ito, M.; Hirakawa, M.; Osaku, A.; Ikariya, T. Organometallics 2003, 22, 4190.
28. These wavenumbers fall in the considerably lower range as compared to the other cationic Cp*Ru(CO) complexes bearing various N-N chelate ligands, although we have to consider various factors including differences of counterions in addition to N-N chelate ligands. (a) Mbaye, M. D.; Demerseman, B.; Renaud, J.-L.; Bruneau, C. J. Organomet. Chem. 2005, 690, 2149.
29. (b) Balavoine, G. G. A.; Boyer, T.; Livage, C. Organometallics 1992, 11, 456.
30. (c) Albers, M. O.; Liles, D. C.; Robinson, D. J.; Singleton, E. Organometallics 1987, 6, 2179.
31. (d) Petrovic, D.; Glöge, T.; Bannenberg, T.; Hrib, C. G.; Randoll, S.; Jones, P. G.; Tamm, M. Eur. J. Inorg. Chem. 2007, 3472.
32. 2 and PN ligands underwent smoothly under thermal conditions. Liu, C.-Y.; Cheng, M.-C.; Peng, S.-M.; Liu, S.-T. Organometallics 1994, 13, 4294.
33. +. Fuentealba, M.; Toupet, L.; Manzur, C.; Carrillo, D.; Ledoux-Rak, I.; Hamon, J.-R. J. Organomet. Chem. 2007, 692, 1099.
34. (a) Stoppioni, P.; Di Vaira, M.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1982, 6, 1147.
35. (b) Landon, S, J.; Brill, T. B. J. Am. Chem. Soc. 1982, 104, 6571.
36. (c) Landon, S. J.; Brill, T. B. Inorg. Chem. 1984, 23, 1266.
37. 2, the hydrogen transfer can be highlighted to allow several oxidative transformations of alcoholic molecules, (a) Ito, M.; Osaku, A.; Kitahara, S.; Hirakawa, M.; Ikariya, T. Tetrahedron Lett. 2003, 44, 7521.
38. (b) Ito, M.; Kitahara, S.; Ikariya, T. J. Am. Chem. Soc. 2005, 127, 6172.
39. (c) Ito, M.; Osaku, A.; Shiibashi, A.; Ikariya, T Org. Lett. 2007, 9, 1821.
40. Ito, M.; Sakaguchi, A.; Kobayashi, C.; Ikariya, T. J. Am. Chem. Soc. 2007, 129, 291.
41. Ito, M.; Koo, L.-W; Himizu, A.; Kobayashi, C.; Sakaguchi, A.; Ikariya, T. to be submitted.
42. Ikariya, T.; Ito, M.; Shiibashi, A.; Otsuka, T. JP 2008177857, 2008.