Reactivity studies of iridiuni(III) porphyrins with methanol in alkaline media

Organometallics

Volumn 29, Issue 6, 2010, Pages 1343-1354

  Cheung, Chi Wai ^a   Fung, Hong Sang ^a   Lee, Siu Yin ^a   Qian, Ying Ying ^a   Chan, Yun Wai ^a   Chan, Kin Shing ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE MEDIA; BOND METATHESIS; DIANIONS; H-BONDS; HIGHER YIELD; MECHANISTIC STUDIES; NUCLEOPHILIC SUBSTITUTIONS; P-TOLYL; PROTON ELIMINATION; TETRAKIS;

METHANOL; PORPHYRINS; REACTION RATES;

IRIDIUM;

EID: 77949444498     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om9008668     Document Type: Article

References (81)

1. Fujita, K.; Yamaguchi, R. Synlett 2005, 4, 560-571.
2. (a) Fujita, K.; Furukawa, S.; Yamaguchi, R. J. Organomet. Chem. 2002, 649, 289-292.
3. (b)Fujita, K.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2002, 4, 2691-2694.
4. (c) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2004, 23, 1490-1492.
5. (d) Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem. Eur. J. 2008, 14, 11474-11479.
6. Fujita, K.; Li, Z.; Ozeki, N.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687-2690.
7. (a) Sakaguchi, S.; Yamaga, T.; Ishii, Y. J. Org. Chem. 2001, 66, 4710-4712.
8. (b) Fujita, K.; Kitatsuji, C.; Furukawa, S.; Yamaguchi, R. Tetrahedron Lett- 2004, 45 3215-3217.
9. (c) Ikariya, T.; Blacker, A. J. Acc. Chem, Res. 2007, 40, 1300-1308.
10. (a) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186-2187.
11. (b) Phillip, J.; Black, P. J.; Edwards, M. G.; Williams, J. M. J. Eur. J. Org. Chem. 2006, 4367-4378.
12. Yamada, T.; Higano, S.; Yano, T.; Yamashita, Y. Chem. Lett. 2009, 38, 40-41.
13. Kumar Mandal, A.; Iqbal, J. Tetrahedron 1997, 53, 7641-7648.
14. Sharma, V. B.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44, 383-386.
15. For examples: (a) Groves, J. T.; Nemo, T. E.; Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032-1033.
16. (b)Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560-564.
17. (c) Lersch, M.; Tilset́, M. Chem. Rev. 2005, 6, 2471-2526.
18. (d) Jones, W. D. Inorg. Chem. 2005, 44, 4475-4484.
19. Li, S.; Cui, W.; Wayland, B. B. Chem. Chem. 2007, 40224-44025
20. (a) Komiya, S.; Srivastava, R. S.; Yamamoto, A.; Yamamoto, T. Organometallcs 1985, 4, 1504-1508.
21. (b) Kawamoto, T.; Fujimura, Y.; Konno. T. Chem. Lett. 2003, 32, 1058-1059.
22. (c) Wender, P. A.; Deschamps, N. M.; Sun, R. Can. J. Chem. 2005, 83, 838-842.
23. (a) Hayashi. Y.: Yamamoto, T.; Yamamoto, A.; Komiya, S.; Yoshihiko, K. J. Am. Chem. Soc. 1986, 108, 385-391.
24. (b) Sjvall, S.; Andersson, C.; Wendt, O. F. Organometallics 2001, 20, 4919-4926.
25. Ohta, T.; Michibata, T.; Yamada, K.; Omori, R.; Furukawa, I. Chem. Commun. 2003, 1192-1193.
26. Nückel, S.; Burger, P. Organometallics 2001, 20, 4345-4359.
27. Thomas, C. M.; Süss-Fink, G. Coord. Chem. Rev. 2003, 243, 125-142.
28. Aldehydic C-H bond, activation of aromatic aldehydes with Rh(ttp)Cl (ttp = 5,10,15,20-tetrakis(p-tolyl)porphyrinato dianion):
29. (a) Chan, K. S.; Lau, C. M.; Yeung, S. K.; Lai, T. H. Organometallics 2007, 26, 1981-1985. Benzylic C-H bond activation of toluenes with Rh(ttp)Cl:
30. (b) Chan, K. S.; Chiu, P. F.; Choi, K. S. Organometallics 2007, 26, 1117-1119. Alkane C-H bond activation with. Rh(ttp)Cl:
31. (c) Chan, Y. W.; Chan, K. S. Organometallics 2008, 27, 4625-4635. Aldehydic C-H bond activation of aromatic aldehydes with. Ir(ttp)Cl(CO):
32. (d) Song, X.; Chan., K. S. Organometallics 2007,26, 965-970. Benzylic C-H bond activation of toluenes with Ir(ttp)Cl(CO):
33. (e) Cheung, C. W.;Chan, K. S. Organometallics 2008, 27, 3043-3055.
34. By Ir(ttp)Cl:
35. (a) Zhang, L.; Chan, K. S. Oreanometallics 2006, 25, 4822-4829. By Ir(ttp)Cl(CO):
36. (b) Li, B.; Chan, K. S. Organometallics 2008, 27, 4034-4042.
37. C-CN bond activation of nitriles with Rh(tmp) radical (tmp = 5.10,15.20-tetrakis(mesityi)porphyrinato dianion):
38. (a) Chan, K. S.: Li, X. Z.; Fung, C. F.; Zhang, L. Organometallics 2007, 26, 20-21.
39. (b) Chan, K. S.; Li, X. Z.; Zhang, L.; Fung, C. F. Organometallics 2007, 26, 2679-2687. C-C bond activation of ethers with Rh(tmp)Cl:
40. (c) Lai, T. H.; Chan, K. S. Organometallics 2009, 28, 6845-6846.
41. Fung, H. S.; Chan, Y. W.; Cheung, C. W.; Choi. K. S.; Lee, S. Y.; Qing, Y. Y.; Chan, K. S. Organometallics 2009, 28, 3981-3989.
42. (a) Yeung, S. K.; Chan, K. S. Organometallics 2005, 24, 6426-6430.
43. (b) Ogoshi, H.; Setsune, J.-I.; Yoshida, Z.-I. J Organomet. Chem. 1978, 759, 317-328.
44. Harkins, S. B.; Peters, J. C. Organometallics 2002, 21,1753-1755.
45. 1H NMR spectroscopic data of both compounds.
46. Collman, J. P.; Chng, L. L.; Tyvoll, D. A. Inorg 1995, 34, 1311-1324.
47. Zhai, H.; Bunn, A.; Wayland, B. B. Chem. Commun. 2001, 1294-1295.
48. 1H NMR spectroscopy.
49. + (δ;(0-phenyl) 7.91 ppm) was selected as the alternative characteristic peak.
50. (a) Tani, K.; Iseki, A.; Yamagata, T. Angew Chem, Chem. Int. End. 1998, 37, 3381-3383.
51. (b) Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Organometallics 2006, 25, 3007-3011.
52. Jiang, B.; Feng, Y.; Ison, E. A. J. Am. Chem. Soc. 2008, 130, 14462-14464.
53. Ofer Blum, O.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 4582-4594.
54. 10
55. Collman, J. P.; Boulatov, R. Inorg. 2001, 40, 560-563.
56. Wayland, B. B.; Vanvoorhees, S. L.; Wilker, C. Inorg. Chem. 1986, 25, 4039-4042.
57. 32
58. Lewis acid can catalyze the reaction of formaldehyde with methanol to give dimethoxymethane. See: Danov, S. M.: Kolesnikov, V. A.; Logutov, I. V. Russ J. Appl.Chem. 2004, 77, 1994-1996.
59. -anion to give Ir-OH has been reported. See: (a) Fulton, J. R.: Holland, A. W.: Fox. D. J.: Bergman, R. G. Acc. Chem. Res. 2002, 35, 44-56.
60. 16e Presumably, the more nucleophilic KOH reacts much more quicldy with Ir(ttp)Cl(CO) to give Ir(ttp)OH.
61. - in basic medium. See: (a) Fu, X.; Basickes, L.; Wayland, B. B. Chem. Commun. 2003, 520-521.
62. (b) Fu, X.; Wayland, B. B. J. Am. Chem. Soc. 2004, 126, 2623-2631.
63. 6 at room temperature in 6 h to give Ir(ttp)D in 77% yield.
64. + 32
65. Sanford, M. S.; Groves, J. T. Angew. Chem. Int. Ed. 2004, 43, 588-590.
66. 3).
67. Mitchell, J. A.; Reid, E. E. J.Am.Cam.Soc. 1931, 53, 1879-1883.
68. 16e
69. a of Ir-H is reported to be higher than that of Rh-H by around 10. Ir(ttp)H is likely to be a weaker acid than Rh(ttp)H. See: Qi, X.-J.: Liu, L.: Fu, Y.; Guo, Q.-X. Organometallics 2006. 25. 5879-5886.
70. aof an acid, the more nucleophilic its conjugate base. See: (a) Bordwell, F. G.; Hughes, D. L. J. Org. Chem. 1983, 48, 2206-2215.
71. (b) Bordwell, F. G.; Hughes, D. L. J. Am. Chem. Soc. 1984, 106, 3234-3240
72. Cui, W.; Wayland, B. B. J. Am. Chem. Soc. 2004, 126, 8266-8274.
73. 3 are about 70 and. 62 kcal/mol, respectively: Wayland, B. B. Personal communication, University of Pennsylvania, Philadelphia, PA, 2007.
74. 3:
75. 3:
76. 3-OH and H-OH:
77. (d) Luo, Y-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2002.
78. Alder, A. D.; Logon, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakof, L. J. Org. Chem. 1967, 32, 476.
79. Chan, K. S.; Mak, K. W.: Tse, M. K.; Yeung. S. K.; Li, B. Z.: Chan. Y. W.J. Organomet. Chem. 2008. 693. 399-407.
80. Wagner, R. W.; Lawrence, D. S.; Lindsey, J. S. Lindsey, J. S. Tetrahedron Lett. 1987, 28, 3069-3070.
81. Farnos, M. D.; Woods, B. A.; Wayland, B. B. J. Am. Chem. Soc. 1986, 108, 3659-3663.