pH-selective synthesis and structures of alkynyl, acyl, and ketonyl intermediates in anti-markovnikov and markovnikov hydrations of a terminal alkyne with a water-soluble iridium aqua complex in water

Journal of the American Chemical Society

Volumn 126, Issue 50, 2004, Pages 16520-16527

  Ogo, Seiji ^a   Uehara, Keiji ^a   Abura, Tsutomu ^a   Watanabe, Yoshihito ^b   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; HYDRATION; ION EXCHANGE; IONIZATION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PH EFFECTS; SEPARATION; SOLUTIONS; SYNTHESIS (CHEMICAL);

CORRELATION SPECTROSCOPY (COSY); DISTORTIONLESS ENHANCEMENT BY POLARIZATION TRANSFER (DEPT); LIGANDS; MARKOVNIKOV HYDRATION;

HYDROCARBONS;

ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYNE; ALKYNYL GROUP; CARBON; HYDROGEN; IRIDIUM COMPLEX; KETONE DERIVATIVE; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; ELECTROSPRAY; HYDRATION; INFRARED RADIATION; ISOLATION PROCEDURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PH MEASUREMENT; POLARIZATION; PROTON TRANSPORT; SEPARATION TECHNIQUE; SOLUBILITY; SYNTHESIS; X RAY ANALYSIS;

EID: 11444269941     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0473541     Document Type: Article

References (56)

1. (a) Joó, F. In Catalysis by Metal Complexes; Aqueous Organometallic Catalysis 23; James, B. R., van Leeuwen, P. W. N. M., Series Eds.; Kluwer Academic Publishers: Dordrecht, 2001; p 300, and references therein,
2. (b) Joó, F. Acc. Chem. Res. 2002, 35, 738-745.
3. (c) Joó, F.; Kovács, J.; Bényei, A. C.; Nadasdi, L.; Laurenczy, G. Chem. Eur. J. 2001, 7, 193-199.
4. (d) Laurenczy, G.; Joó, F.; Nadasdi, L. Inorg. Chem. 2000, 39, 5083-5088.
5. (e) Joó, F.; Kovács, J.; Kathó, A.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45.
6. (f) Joó, F.; Kovács, J.; Bényei, A. C.; Kathó, Á. Angew. Chem., Int. Ed. 1998, 37, 969-970.
7. (a) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis: Concept and Applications, 2nd & rev. ed.; Wiley-VCH: Weinheim, Germany, 2004; p 750.
8. (b) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
9. (a) Süss-Fink, G.; Faure, M.; Ward, T. R. Angew. Chem., Int. Ed. 2002, 41, 99-101.
10. (b) Cherioux, F.; Maisse-Francois, A.; Neels, A.; Stoeckli-Evans, H.; Süss-Fink, G. J. Chem. Soc., Dalton Trans. 2001, 14, 2184-2187.
11. (c) Süss-Fink, G.; Meister, G.; Haak, S.; Rheinwald, G.; Stoeckli-Evans, H. New J. Chem. 1997, 21, 785-790.
12. (d) Süss-Fink, G.; Meister, A.; Meister, G. Coord. Chem. Rev. 1995, 143, 97-111.
13. (a) Salignac, B.; Grundler, P. V.; Cayemittes, S.; Frey, U.; Scopelliti, R.; Merbach, A. E.; Hedinger, R.; Hegetschweiler, K.; Alberto, R.; Prinz, U.; Raabe, G.; Koelle, U.; Hall, S. Inorg. Chem. 2003, 42, 3516-3526.
14. (b) Koelle, U.; Goerissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911-917.
15. (c) Dadci, L.; Elias, H.; Frey, U.; Hoernig, A.; Koelle, U.; Merbach, A. E.; Paulus, H.; Schneider, J. S. Inorg. Chem. 1995, 34, 306-315.
16. (d) Koelle, U. Coord. Chem. Rev. 1994, 135/136, 623-650.
17. (e) Koelle, U. New J. Chem. 1992, 16, 157-169.
18. (f) Koelle, U.; Flunkert, G.; Goerissen, R.; Schmidt, M. U.; Englert, U. Angew. Chem., Int. Ed. Engl. 1992, 31, 440-442.
19. (g) Koelle, U.; Fuss, B. Chem. Ber. 1984, 117, 753-762.
20. (a) Ogo, S.; Uehara, K.; Abura, T.; Watanabe, Y.; Fukuzumi, S. Organo-metallics 2004, 23, 3047-3052.
21. (b) Ogo, S.; Uehara, K.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 3020-3021.
22. (c) Hayashi, H.; Ogo, S.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 14266-14267.
23. (d) Abura, T.; Ogo, S.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 4149-4154.
24. (e) Ogo, S.; Nakai, H.; Watanabe, Y. J. Am. Chem. Soc. 2002, 124, 597-601.
25. (f) Ogo, S.; Abura, T.; Watanabe, Y. Organometallics 2002, 21, 2964-2969.
26. Li, C.-J.; Chan, T.-H. In Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; p 199 and references therein.
27. Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water, Grieco, P. A., Ed.:, Thomson Science: London, 1998; p 310 and references therein.
28. Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1998, 37, 2867-2869.
29. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
30. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
31. (a) Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Org. Lett. 2001, 3, 735-737.
32. (b) Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917-11924.
33. Grotjahn, D. B.; Incarvito, C. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 2001, 40, 3884-3886.
34. (a) Arikawa, Y.; Nishimura, Y.; Kawano, H.; Onishi, M. Organometallics 2003, 22, 3354-3356.
35. (b) Arikawa, Y.; Nishimura, Y.; Ikeda, K.; Onishi, M. J. Am. Chem. Soc. 2004, 126, 3706-3707.
36. Suzuki, T.; Tokunaga, M.; Wakatsuki, Y. Tetrahedron Lett. 2002, 43, 7531-7533.
37. Alvarez, P.; Bassetti, M.; Gimeno, J.; Mancini, G. Tetrahedron Lett. 2001, 42, 8647-8470.
38. Alessandro, N. D.; Deo, M. D.; Bonetti, M.; Tonucci, L.; Morvillo, A.; Bressan, M. Eur. J. Inorg. Chem. 2004, 810-817.
39. Ogo, S.; Makihara, N.; Kaneko, Y.; Watanabe, Y. Organometallics 2001, 20, 4903-4910.
40. (a) Glasoe P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
41. (b) Mikkelsen, K.; Nielsen, S. O. J. Phys. Chem. 1960, 64, 632-637.
42. Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585-4594.
43. Bianchini, C.; Peruzzini, M.; Zanobini, F.; Lopez, C.; de los Rios, I.; Romerosa, A. Chem. Commun. 1999, 443-444.
44. Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; García-Granda, S. Organometallics 1999, 18, 2821-2832.
45. Baya M.; Crochet, P.; Esteruelas, M. A.; Lópes, A. M.; Modrego, J.; Oñate, E. Organometallics, 2001, 20, 4291-4294.
46. del Río, I.; Gossage, R. A.; Hannu, M. S.; Lutz, M.; Spek, A. L.; van Koten, G. Organometallics 1999, 18, 1097-1105.
47. Katayama, H.; Wada, C.; Taniguchi, K.; Ozawa, F. Organometallics 2002, 21, 3285-3291.
48. (a) Bustelo, E.; Carbó, J. J.; Lledós, A.; Mereiter, K.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 2003, 125, 3311-3321.
49. (b) Aneetha, H.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Mereiter, K. Organometallics 2003, 22, 2001-2013.
50. (c) Tenorio, M. A. J.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. Organometallics 2000, 19, 1333-1342.
51. (d) Bustelo, E.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 950-951.
52. (e) de los Ríos, I.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529-6538.
53. Menéndez, C.; Morales, D.; Pérez, J.; Riera, V.; Miguel, D. Organometallics 2001, 20, 2775-2781.
54. Carmona, D.; Vega, C.; Lahoz, F. J.; Atencio, R.; Oro, L. A.; Lamata, M. P.; Viguri, p.; José, E. S. Organometallics 2000, 19, 2273-2280.
55. Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79-154.
56. The isotopic labeling experiments were carried out at 0°C to avoid the back-reaction of 2 with protons.