Ruthenium-catalyzed novel carbon-carbon bond forming reactions via ruthenium-allenylidene complexes

Current Organic Chemistry

Volumn 10, Issue 2, 2006, Pages 135-150

  Nishibayashi, Yoshiaki ^a   Uemura, Sakae ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

1,3 cyclohexanedione; Alkylation; Carbon centered nucleophiles; Heteroaromatic compound; Propargylic alcohols

Indexed keywords

ACETONE; ALCOHOLS; ALKYLATION; CATALYSIS; NUCLEOPHILES; REACTION INTERMEDIATES; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

1,3-CYCLOHEXANEDIONE; ALLENYLIDENE COMPLEXES; CARBON-CARBON BOND-FORMING REACTIONS; CARBON-CENTERED NUCLEOPHILE; DIRUTHENIUM COMPLEX; HETEROAROMATIC COMPOUNDS; HYDROXYL GROUPS; ORGANIC SYNTHESIS; PROPARGYLIC ALCOHOLS; THIOLATES;

CARBON;

ACETONE; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALLENE DERIVATIVE; AROMATIC COMPOUND; BRIDGED COMPOUND; CARBON; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYL GROUP; KETONE DERIVATIVE; NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND; PHENOL DERIVATIVE; RUTHENIUM COMPLEX;

ALKYLATION; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; CYCLOADDITION; ORGANIC CHEMISTRY; REACTION ANALYSIS; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33646074054     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206775192960     Document Type: Review

References (65)

1. (a) Fischer, E. O.; Kalder, H-J.; Frank, A.; Kohler, H.; Huttner, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 623.
2. (b) Berke, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 624.
3. Selegue, J. P. Organometallics 1982, 1, 217.
4. (a) Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 1998, 178-180, 409.
5. (b) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
6. (c) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
7. For recent reviews, see: (a) Winter, R. F.; Zális, S. Coord. Chem. Rev. 2004, 248, 1565.
8. (b) Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 2004, 248, 1585.
9. (c) Cadierno, V.; Gamasa, M.P.; Gimeno, J. Coord. Chem. Rev. 2004, 248, 1627.
10. (a) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreno, E.; García-Granda, S. Organometallics 2001, 20, 3175.
11. (b) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Favello, L. R.; Llusar, R. M. Organometallics 2002, 21, 3716.
12. (c) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J. Organometallics 2002, 21, 3837.
13. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreno, E.; García-Granda, S. J. Organomet. Chem. 2003, 670, 75.
14. (e) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J. Dalton Trans. 2003, 3060.
15. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207 and references therein.
16. (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, G. A.; Wilkinson, G., Eds.; Pergamon, New York, 1995; Vol. 12, Chapter 7.1.
17. (c) Green, J. R. Curr. Org. Chem. 2001, 5, 809.
18. (a) Conejero, S.; Díez, J.; Gamasa, M. P.; Gimeno, J.; García-Granda, S. Angew. Chem. Int. Ed. 2002, 41, 3439.
19. (b) Baya, M.; Buil, M. L.; Esteruelas, M. A.; López, A. M.; Oñate, E.; Rodríguez, J. R. Organometallics 2002, 21, 1841.
20. For recent examples, see: (a) Trost, B. M.; Flygare, J. A. J. Am. Chem. Soc. 1992, 114, 5476.
21. (b) Maddock, S. M.; Finn, M. G. Angew. Chem. Int. Ed. 2001, 40, 2138.
22. (c) Yeh, K.-L.; Liu, B.; Lo, H.-L.; Huang, H.-L.; Liu, R.-S. J. Am. Chem. Soc. 2002, 124, 6510.
23. (d) Datta, S.; Chang, C.-L.; Yeh, K.-L.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 9294.
24. (e) Cadierno, V.; Díez, J.; García-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 2716.
25. (a) The thiolate-bridged diruthenium complexes have been found to provide unique bimetallic reaction sites for activation and transformation of various terminal alkynes, see: Nishibayashi, Y.; Yamanashi, M.; Wakiji, I.; Hidai, M. Angew. Chem. Int. Ed. 2000, 39, 2909 and references therein.
26. 2RuCp·Cl] (1a) is commercially available from Wako Pure Chemical Industries (Japan) as met-DIRUX (methanethiolate-bridged diruthenium complex) (130-14581).
27. (a) Nishibayashi, Y.; Wakiji, I.; Hidai, M. J. Am. Chem. Soc. 2000, 122, 11019.
28. (b) Inada, Y.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 15172.
29. (c) Nishibayashi, Y.; Milton, M. D.; Inada, Y.; Yoshikawa, M.; Wakiji, I.; Hidai, M.; Uemura, S. Chem. Eur. J. 2005, 11, 1433.
30. For reviews, see: (a) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons; New York, 1995.
31. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
32. (c) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8E.
33. Nishibayashi, Y.; Wakiji, L.; Ishii, Y.; Uemura, S.; Hidai, M. J. Am. Chem. Soc. 2001, 123, 3393.
34. (a) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759.
35. (b) Braun, M.; Laicher, F.; Meier, T. Angew. Chem. Int. Ed. Engt. 2000, 39, 3494.
36. Kimura, M.; Horino, Y.; Mukai, R.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2001, 123, 10401.
37. Nicholas, K. M.; Mulvaney, M.; Bayer, M. J. Am. Chem. Soc. 1980, 102, 2508.
38. (a) Saito S.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 611.
39. (b) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
40. (a) Nishibayashi, Y.; Imajima, H.; Onodera, G.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 26.
41. (b) Nishibayashi, Y.; Imajim, H.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 5100.
42. (a) Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181.
43. (b) Yoshikai, N.; Nakamura, E. Adv. Synth. Catal. 2003, 345, 1159.
44. Ammal, S. C.; Yoshikai, N.; Inada, Y.; Nishibayashi, Y.; Nakamura, E. J Am. Chem. Soc. 2005, 127, 9428.
45. Caffyn, A. J. M.; Nicholas, K. M. J. Am. Chem. Soc. 1993, 115, 6438.
46. Nishibayashi, Y.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2003, 22, 873.
47. Nishibayashi, Y.; Uemura S. unpublished results.
48. Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Org. Chem. 2004, 69, 3408.
49. Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846.
50. + with N-methylpyrrole was found to give an allenylidene complex with N-methylpyrrole attaffing at γ carbon, but no example of the reaction of allenylidene complexes with aromatic compounds has been reported until now; Bruce, M. I.; Hinterding, P.; Low, P. J.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 1009.
51. (b) Touchard, D.; Haquette, P.; Daridor, A.; Toupet, L.; Dixneuf, P. H. J. Am. Chem. Soc. 1994, 116, 11157.
52. + with pyrrole was found to give a vinylidene complex with pyrrole formally attacking at γ-carbon, but no example of the direct reaction of an allenylidene complex with aromatic compounds has been reported until now; Bustelo, E.; Jiménez-Tenorio, M.; Mereiter, K.; Puerta, M. C.; Valerga, P. Organometallics 2002, 21, 1903.
53. Roth, K.-D. Synlett 1993, 529.
54. (a) Kuhn, O.; Rau, D.; Mayr, H. J Am. Chem. Soc. 1998, 120, 900.
55. (b) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500.
56. (c) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.
57. Nishibayashi, Y.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 7900.
58. Tanaka, K.; Aoki, H.; Hosomi, H.; Ohba, S. Org. Lett. 2000, 2, 2133.
59. Baya, M.; Buil, M. L.; Esteruelas, M. A.; López, A. M.; Oñate, E.; Rodríguez, J. R. Organometallics 2002, 21, 1841.
60. Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 6060.
61. Mann, A.; Muller, C.; Tyrrell, E. J. Chem. Soc., Perkin Trans. I 1998, 1427.
62. Matsuda, I.; Komori, K.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 9072.
63. Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 15760.
64. Kennedy-Smith, J. J.; Young, L. A.; Toste, F. D. Org. Lett. 2004, 6, 1325.
65. Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem. Int. Ed. 2003, 42, 1495.