Iridium-catalyzed arene ortho -silylation by formal hydroxyl-directed C-H activation

Journal of the American Chemical Society

Volumn 132, Issue 48, 2010, Pages 17092-17095

  Simmons, Eric M ^a   Hartwig, John F ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL KETONES; BENZYL ALCOHOL; C-H ACTIVATION; CARBONYL COMPOUNDS; CH-BOND ACTIVATION; CROSS-COUPLINGS; DEHYDROGENATIVE CYCLIZATION; HYDROGEN ACCEPTOR; HYDROXYL GROUPS; NORBORNENES; ONE POT; ORTHO-SILYLATION; PHENANTHROLINES; SILYL ETHERS; SILYLATIONS; SYNTHETIC UTILITY;

ACTIVATION ANALYSIS; ALDEHYDES; CARBONYLATION; CATALYSIS; ETHERS; KETONES; PHENOLS;

IRIDIUM;

BENZALDEHYDE; BENZYL ALCOHOL; CARBON; FLUORIDE; HYDROGEN; HYDROXIDE; HYDROXYL GROUP; IRIDIUM; KETONE DERIVATIVE; NORBORNENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; CYCLIZATION; DEHYDROGENATION; ONE POT SYNTHESIS; OXIDATION; SILYLATION;

CARBON; CATALYSIS; HYDROCARBONS, AROMATIC; HYDROGEN; HYDROXIDES; INDIUM; SILANES;

EID: 78650100824     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1086547     Document Type: Article

References (76)

1. For general C-H activation reviews, see
2. Dick, A. R. and Sanford, M. S. Tetrahedron 2006, 62, 2439-2463
3. Activation and Functionalization of C-H Bonds; Goldberg, K. I. and Goldman, A. S., Eds.; American Chemical Society: Washington, DC, 2004; Vol. 885.
4. Kakiuchi, F. and Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101
5. Shilov, A. E. and Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932
6. For recent applications of C-H activation with main group reagents to complex molecule synthesis, see
7. Fischer, D. F. and Sarpong, R. J. Am. Chem. Soc. 2010, 132, 5926-5927
8. Tomita, D., Yamatsugu, K., Kanai, M., and Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946-6948
9. Beck, E. M., Hatley, R., and Gaunt, M. J. Angew. Chem., Int. Ed. 2008, 47, 3004-3007 For general reviews of strategic use of C-H activation in synthesis, see: Ishihara, Y. and Baran, P. S. Synlett 2010, 1733-1745
10. Godula, K. and Sames, D. Science 2006, 312, 67-72
11. Gustavson, W. A., Epstein, P. S., and Curtis, M. D. Organometallics 1982, 1, 884-885
12. Sakakura, T., Tokunaga, Y., Sodeyama, T., and Tanaka, M. Chem. Lett. 1987, 2375-2378
13. For examples using hydrosilanes, see
14. Kakiuchi, F., Igi, K., Matsumoto, M., Chatani, N., and Murai, S. Chem. Lett. 2001, 422-423
15. Kakiuchi, F., Igi, K., Matsumoto, M., Hayamizu, T., Chatani, N., and Murai, S. Chem. Lett. 2002, 396-397
16. Kakiuchi, F., Matsumoto, M., Tsuchiya, K., Igi, K., Hayamizu, T., Chatani, N., and Murai, S. J. Organomet. Chem. 2003, 686, 134-144
17. Ihara, H. and Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502-7503 For examples using other silane species, see: Kakiuchi, F., Matsumoto, M., Sonoda, M., Fukuyama, T., Chatani, N., Murai, S., Furukawa, N., and Seki, Y. Chem. Lett. 2000, 750-751
18. Tobisu, M., Ano, Y., and Chatani, N. Chem.-Asian J. 2008, 3, 1585-1591
19. Tsukada, N. and Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 5022-5023
20. Boebel, T. A. and Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534-7435 For an extension of this approach to the silylation of indoles, see: Robbins, D. W., Boebel, T. A., and Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068-4069
21. For recent examples of hydroxyl-directed C-H bond activation, see
22. Wang, X., Lu, Y., Dai, H.-X., and Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203-12205
23. Watson, A. J. A., Maxwell, A. C., and Williams, J. M. J. Org. Lett. 2010, 12, 3856-3859
24. Lu, Y., Wang, D.-H., Engle, K. M., and Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916-5921
25. For previous examples of structurally related benzoxasiloles, see
26. Ando, W., Sekiguchi, A., and Migita, T. J. Am. Chem. Soc. 1975, 97, 7159-7160
27. Ando, W. and Sekiguchi, A. J. Organomet. Chem. 1977, 133, 219-230
28. Ando, W., Ikeno, M., and Sekiguchi, A. J. Am. Chem. Soc. 1977, 99, 6447-6449
29. Kang, K. T., Song, H. Y., and Seo, H. C. Chem. Lett. 1985, 617-620
30. Farnham, W. B., Dixon, D. A., Middleton, W. J., Calabrese, J. C., Harlow, R. L., Whitney, J. F., Jones, G. A., and Guggenberger, L. J. J. Am. Chem. Soc. 1987, 109, 476-483
31. Yamamoto, Y., Takeda, Y., and Akiba, K. Tetrahedron Lett. 1989, 30, 725-728
32. Sieburth, S. M. and Fensterbank, L. J. Org. Chem. 1992, 57, 5279-5281
33. Belzner, J., Ihmels, H., Pauletto, L., and Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319
34. Fitch, J. W., Cassidy, P. E., and Ahmed, M. J. J. Organomet. Chem. 1996, 522, 55-57
35. Hijji, Y. M., Hudrlik, P. F., and Hudrlik, A. M. Chem. Commun. 1998, 1213-1214
36. Studer, A. and Steen, H. Chem.-Eur. J. 1999, 5, 759-773
37. Hudrlik, P. F., Arango, J. O., Hijji, Y. M., Okoro, C. O., and Hudrlik, A. M. Can. J. Chem. 2000, 78, 1421-1427
38. Bashiardes, G., Chaussebourg, V., Laverdan, G., and Pornet, J. Chem. Commun. 2004, 122-123
39. Chouraqui, G. l., Petit, M., Aubert, C., and Malacria, M. Org. Lett. 2004, 6, 1519-1521
40. Levin, S., Nani, R. R., and Reisman, S. E. Org. Lett. 2010, 12, 780-783
41. For the use of benzoxasiloles as reusable aryl and alkenyl transfer agents, see
42. Nakao, Y., Imanaka, H., Sahoo, A. K., Yada, A., and Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952-6953
43. Nakao, Y., Sahoo, A. K., Yada, A., Chen, J. S., and Hiyama, T. Sci. Technol. Adv. Mater. 2006, 7, 536-543
44. Nakao, Y., Imanaka, H., Chen, J. S., Yada, A., and Hiyama, T. J. Organomet. Chem. 2007, 692, 585-603
45. Nakao, Y., Ebata, S., Chen, J. S., Imanaka, H., and Hiyama, T. Chem. Lett. 2007, 36, 606-607
46. Nakao, Y., Chen, J., Imanaka, H., Hiyama, T., Ichikawa, Y., Duan, W.-L., Shintani, R., and Hayashi, T. J. Am. Chem. Soc. 2007, 129, 9137-9143
47. Nakao, Y., Chen, J., Tanaka, M., and Hiyama, T. J. Am. Chem. Soc. 2007, 129, 11694-11695
48. Shintani, R., Ichikawa, Y., Hayashi, T., Chen, J., Nakao, Y., and Hiyama, T. Org. Lett. 2007, 9, 4643-4645
49. Nakao, Y., Takeda, M., Chen, J. S., Hiyama, T., Ichikawa, Y., Shintani, R., and Hayashi, T. Chem. Lett. 2008, 37, 290-291
50. Nakao, Y., Takeda, M., Chen, J., and Hiyama, T. Synlett 2008, 774-776
51. Jones, G. R. and Landais, Y. Tetrahedron 1996, 52, 7599-7662
52. Denmark, S. E. and Regens, C. S. Acc. Chem. Res. 2008, 41, 1486-1499
53. Denmark, S. E. and Sweis, R. F. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; De Meijere, A. and Diederich, F., Eds.; Wiley-VCH: New York, 2004; pp 163 - 216.
54. Hiyama, T. and Shirakawa, E. In Cross-Coupling Reactions; Miyaura, N., Ed.; Springer: Berlin/Heidelberg, 2002; Vol. 219, pp 61 - 85.
55. Field, L. D., Messerle, B. A., Rehr, M., Soler, L. P., and Hambley, T. W. Organometallics 2003, 22, 2387-2395
56. 2, see
57. Reyes, C., Prock, A., and Giering, W. P. J. Organomet. Chem. 2003, 671, 13-26
58. Ojima, I., Kogure, T., Kumagai, M., Horiuchi, S., and Sato, T. J. Organomet. Chem. 1976, 122, 83-97
59. Mkhalid, I. A. I., Barnard, J. H., Marder, T. B., Murphy, J. M., and Hartwig, J. F. Chem. Rev. 2010, 110, 890-931
60. The accelerating effect of norbornene on Ir-catalyzed C-H activation has been observed previously; see
61. Lu, B. and Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508-7510
62. Lu, B. and Falck, J. R. J. Org. Chem. 2010, 75, 1701-1705
63. 2, in line with previous observations (see ref 6a).
64. The benzoxasilole products derived from primary silyl ethers proved sensitive to silica gel chromatography but were readily purified by bulb-to-bulb distillation of the concentrated reaction mixture.
65. For recent examples of arene ortho -oxygenation by directed C-H activation, see
66. Zhang, Y.-H. and Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654-14655
67. Desai, L. V., Malik, H. A., and Sanford, M. S. Org. Lett. 2006, 8, 1141-1144
68. Dick, A. R., Hull, K. L., and Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301
69. For arene ortho -oxygenation by a directed ortho -lithiation/silylation/ oxidation sequence, see
70. Bracegirdle, S. and Anderson, E. A. Chem. Commun. 2010, 46, 3454-3456
71. For previous examples of fluoride-free Tamao-Fleming oxidation, see: (a) Reference 19.
72. Tamao, K. and Ishida, N. J. Organomet. Chem. 1984, 269, c37-c39
73. Snieckus, V. Chem. Rev. 1990, 90, 879-933
74. See the Supporting Information for details.
75. For the NaOH-promoted cross-coupling of aryl- and alkenyl(dichloro) silanes, in which in situ generated organosilanolates are likely intermediates, see
76. Hagiwara, E., Gouda, K.-i., Hatanaka, Y., and Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442