Ruthenium-catalyzed formation of aryl(diphenyl)phosphine oxides by reactions of propargylic alcohols with diphenylphosphine oxide

Organic Letters

Volumn 7, Issue 18, 2005, Pages 4029-4032

  Onodera, Gen ^a   Matsumoto, Hideyuki ^a   Milton, Marilyn Daisy ^a   Nishibayashi, Yoshiaki ^b   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944504049     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0515311     Document Type: Article

References (25)

1. (a) Nishibayashi, Y.; Wakiji, I.; Hidai, M. J. Am. Chem. Soc. 2000, 122, 11019.
2. (b) Nishibayashi, Y.; Wakiji, I.; Ishii, Y.; Uemura, S.; Hidai, M. J. Am. Chem. Soc. 2001, 123, 3393.
3. (c) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846.
4. (d) Inada, Y.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 15172.
5. (e) Nishibayashi, Y.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2003, 22, 873.
6. (f) Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem., Int. Ed. 2003, 42, 1495.
7. (g) Nishibayashi, Y.; Milton, M. D.; Inada, Y.; Yoshikawa, M.; Wakiji, I.; Hidai, M.; Uemura, S. Chem. Eur. J. 2005, 11, 1433.
8. (h) Ammal, S. C.; Yoshikai, N.; Inada, Y.; Nishibayashi, Y.; Nakamura, E. J. Am. Chem. Soc.2005, 127, 9428.
9. (a) The thiolate-bridged diruthenium complexes were found to provide a unique bimetallic reaction site 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.
10. (b) Nishibayashi, Y.; Imajima, H.; Onodera, G.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 26.
11. (c) Nishibayashi, Y.; Imajima, H.; Onodera, G.; Inada, Y.; Hidai, M.; Uemura, S. Organometallics 2004, 23, 5100.
12. (d) The methanethiolate-bridged diruthenium complexes are commercially available from Wako Pure Chemical Industries (Japan) as met-DIRUX (methanethiolate-bridged diruthenium complex) (1a) (130-14581) and met-DIRUX-OTf (1e) (132-14781).
13. Milton, M. D.; Onodera, G.; Nishibayashi, Y.; Uemura, S. Org. Lett. 2004, 6, 3993.
14. The propargylic alcohol 3a can react with various nucleophiles to afford the corresponding propargylic substituted products; see refs 1b-d,f,g.
15. Typical results are shown in Supporting Information as Table S1.
16. An ORTEP drawing of 4a is shown in Supporting Information as Figure S1.
17. The isomerization of propargylic phosphine oxide to allenyl phosphine oxide was observed, and allenyl phosphine oxide can be isolated; see ref 3.
18. Ab initio molecular orbital calculations of A and 8 were carried out.
19. (a) Mukai and co-workers reported an endo-mode ring-closing reaction of allenyl phosphine oxides: Mukai, C.; Ohta, M.; Yamashita, H.; Kitagaki, S. J. Org. Chem. 2004, 69, 6867.
20. (b) Maynard and co-workers reported a similar endo-mode ring-closing reaction: Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031.
21. (c) Michael-type exo-mode ring-closing reactions have also been reported: Brel, V. K. Synthesis 2001, 1539.
22. (a) Coumbe, T.; Lawrence, N. J.; Muhammad, F. Tetrahedron Lett. 1994, 35, 625.
23. (b) Allen, A., Jr.; Ma, L.; Lin, W. Tetrahedron Lett. 2002, 43, 3707.
24. For a recent example, see: Oestreich, M.; Schmid, U. K.; Auer, G.; Keller, M. Synthesis 2003, 2725.
25. 2 is found to work as a highly efficient catalyst for the Heck vinylation of aryl halides: Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.