Isolation and crystal structures of both enol and keto tautomer intermediates in a hydration of an alkyne-carboxylic acid ester catalyzed by iridium complexes in water

Journal of the American Chemical Society

Volumn 130, Issue 50, 2008, Pages 17141-17147

  Kanemitsu, Hironobu ^a,b   Uehara, Keiji ^c   Fukuzumi, Shunichi ^c   Ogo, Seiji ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AQUA COMPLEXES; BIPYRIDINE; CATALYTIC HYDRATIONS; CORRELATION SPECTROSCOPIES; COUNTER ANIONS; DISTORTIONLESS ENHANCEMENT BY POLARIZATION TRANSFERS; ELECTROSPRAY IONIZATION MASS SPECTROMETRIES; ETHYL ESTERS; IRIDIUM COMPLEXES; KETO ACIDS; NMR STUDIES; RAY ANALYSES; REACTION TIMES; SUCCESSFUL ISOLATIONS;

ACETYLENE; ACIDS; BIOLOGICAL MATERIALS; CARBOXYLIC ACIDS; ELECTROSPRAY IONIZATION; ESTERIFICATION; ESTERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRATION; IONIZATION OF LIQUIDS; IRIDIUM COMPOUNDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ORGANIC ACIDS; ORGANIC COMPOUNDS;

IRIDIUM;

EID: 58049218932     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807254d     Document Type: Article

References (36)

1. (a) Torst, B. M. Science 1991, 254, 1471-1477.
2. (b) Torst, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
3. (c) Torst, B. M. Acc. Chem. Res. 2002, 35, 695-705.
4. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
5. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
6. Hintermann, L.; Labonne, A. Synthesis 2007, 8, 1121-1150.
7. (a) Halpern, J.; James, B. R.; Kemp, A. L. W. J. Am. Chem. Soc. 1961, 83, 4097-4098.
8. (b) Halpern, J.; James, B. R.; Kemp, A. L. W. J. Am. Chem. Soc. 1966, 88, 5142-5147.
9. Khan, M. M. T.; Halligudi, S. B.; Shukla, S. J. Mol. Catal. 1990, 58, 299-305.
10. Menashe, N.; Shvo, Y. J. Org. Chem. 1993, 58, 7434-7439.
11. James, B. R.; Rempel, G. L. J. Am. Chem. Soc. 1969, 91, 863-865.
12. Blum, J.; Huminer, H.; Alper, H. J. Mol. Catal. 1992, 75, 153-160.
13. Avshu, A.; O'Sullivan, R. D.; Parkins, A. W.; Alcock, N. W.; Countryman, R. M. J. Chem. Soc., Dalton Trans. 1983, 1619-1624.
14. (a) Hiscox, W.; Jennings, P. W. Organometallics 1990, 9, 1997-1999.
15. (b) Jennings, P. W.; Hartman, J. W.; Hiscox, W. C. Inorg. Chim. Acta 1994, 222, 317-322.
16. Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237-4245.
17. (a) Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127-3130.
18. (b) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
19. Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1418.
20. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563-1565.
21. Easton, N. R.; Cassady, D. R.; Dillard, R. D. J. Org. Chem. 1965, 30, 3084-3088.
22. Damiano, J. P.; Postel, M. J. Organomet. Chem. 1996, 522, 303-305.
23. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, 4th ed.; John Wiley & Sons: New York, 1992; p 762.
24. (a) Matsumoto, K.; Nagai, Y.; Matsunami, J.; Mizuno, K.; Abe, T.; Somazawa, R.; Kinoshita, J.; Shimura, H. J. Am. Chem. Soc. 1998, 120, 2900-2907.
25. (b) Ochiai, M.; Lin, Y. S.; Yamada, J.; Misawa, H.; Arai, S.; Matsumoto, K. J. Am. Chem. Soc. 2004, 126, 2536-2545.
26. (a) Arikawa, Y.; Nishimura, Y.; Kawano, H.; Onishi, M. Organometallics 2003, 22, 3354-3356.
27. (b) Arikawa, Y.; Nishimura, Y.; Ikeda, K.; Onishi, M. J. Am. Chem. Soc. 2004, 126, 3706-3707.
28. (c) Nishimura, Y.; Ikeda, K.; Inoue, T.; Onishi, M. Dalton Trans. 2005, 5, 930-937.
29. Ogo, S.; Uehara, K.; Abura, T.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 16520-16527.
30. Harman, W. D.; Dobson, J. C.; Taube, H. J. Am. Chem. Soc. 1989, 111, 3061-3062.
31. Woerpel, K. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 7888-7889.
32. Casado, R.; Contel, M.; Laguna, M.; Romero, P.; Snaz, S. J. Am. Chem. Soc. 2003, 125, 11925-11935.
33. Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903-1910.
34. (a) Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
35. (b) Mikkelsen, K.; Nielsen, S. O. J. Phys. Chem. 1960, 64, 632-637.
36. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed.; Wiley: New York, 1997, and references therein.