Room-temperature regioselective c-H/olefin coupling of aromatic ketones using an activated ruthenium catalyst with a carbonyl ligand and structural elucidation of key intermediates

Journal of the American Chemical Society

Volumn 132, Issue 50, 2010, Pages 17741-17750

  Kakiuchi, Fumitoshi ^a   Kochi, Takuya ^a   Mizushima, Eiichiro ^b   Murai, Shinji ^c  

^a KEIO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONES; ACTIVATED COMPLEX; ALKYLATION PRODUCTS; AROMATIC KETONES; C-C BOND FORMATION; C-H BOND CLEAVAGE; CARBONYL LIGAND; CATALYTIC ACTIVITY; CATALYZED REACTIONS; FIRST ORDER KINETICS; FIRST-ORDER DEPENDENCE; GEOMETRIC ISOMER; ISOLATED YIELD; ISOTOPE LABELING; MECHANISTIC STUDIES; NMR STUDIES; RATE-LIMITING STEPS; REDUCTIVE ELIMINATION; REFLUXING; REGIO-SELECTIVE; ROOM TEMPERATURE; RUTHENIUM CATALYSTS; RUTHENIUM COMPLEXES; STRUCTURAL ELUCIDATION;

AROMATIC COMPOUNDS; ELECTROCHEMICAL SENSORS; ISOMERS; ISOTOPES; KETONES; OLEFINS; REACTION INTERMEDIATES; RUTHENIUM; RUTHENIUM COMPOUNDS; TOLUENE;

CATALYST ACTIVITY;

2' METHYLACETOPHENONE; ACETOPHENONE; ALKENE; CARBONYL DERIVATIVE; KETONE; RUTHENIUM COMPLEX; SILANE DERIVATIVE; TOLUENE; TRIMETHYLVINYLSILANE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOTOPE LABELING; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 78650297370     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja104918f     Document Type: Article

References (145)

1. Crabtree, R. H. Chem. Rev. 1985, 85, 245-245
2. Guari, Y., Sabo-Etienne, S., and Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047-1055
3. Kakiuchi, F. and Murai, S. Top. Organomet. Chem. 1999, 3, 47-79
4. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
5. Crabtree, R. H. Dalton Trans. 2001, 2437-2450
6. Ritleng, V., Sirlin, C., and Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770
7. Labinger, J. A. and Bercaw, J. E. Nature 2002, 417, 507-514
8. Kakiuchi, F. and Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101
9. Kakiuchi, F. and Chatani, N. Top. Organomet. Chem. 2004, 11, 45-79
10. Park, Y. J. and Jun, C.-H. Bull. Korean Chem. Soc. 2005, 26, 871-877
11. Godula, K. and Sames, D. Science 2006, 312, 67-72
12. Dick, A. R. and Sanford, M. S. Tetrahedron 2006, 62, 2439-2463
13. Alberico, D., Scott, M. E., and Lautens, M. Chem. Rev. 2007, 174-238
14. Kakiuchi, F. Top. Organomet. Chem. 2007, 24, 1-33
15. Matsumoto, T. Catal. Surv. Asia 2007, 11, 31-48
16. Kakiuchi, F. and Kochi, T. Synthesis 2008, 3013-3039
17. Lewis, J. C., Bergman, R. G., and Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013-1025
18. Foley, N. A., Lee, J. P., Ke, Z., Gunnoe, T. B., and Cundari, T. R. Acc. Chem. Res. 2009, 42, 585-597
19. Chen, X., Engle, K. M., Wang, C.-H., and Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
20. Jazzar, R., Hitce, J., Renaudat, A., Sofack-Kreutzer, J., and Baudoin, O. Chem.-Eur. J. 2010, 16, 2654-2674
21. Colby, D. A., Bergman, R. G., and Ellman, J. A. Chem. Rev. 2010, 110, 624-655
22. Dobereiner, G. E. and Crabtree, R. H. Chem. Rev. 2010, 110, 681-703
23. Doyle, M. P., Duffy, R., Ratnikov, M., and Zhou, L. Chem. Rev. 2010, 110, 704-724
24. Willis, M. C. Chem. Rev. 2010, 110, 725-748
25. Sehnal, P., Taylor, J. K., and Fairlamb, I. J. Chem. Rev. 2010, 110, 824-889
26. Lyons, T. W. and Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
27. Selected results from our group
28. Murai, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., and Chatani, N. Nature 1993, 366, 529-531
29. Murai, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., and Chatani, N. Pure Appl. Chem. 1994, 66, 1527-1534
30. Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., Chatani, N., and Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62-83
31. Kakiuchi, F., Yamauchi, M., Chatani, N., and Murai, S. Chem. Lett. 1996, 111-112
32. Sonoda, M., Kakiuchi, F., Chatani, N., and Murai, S. Bull. Chem. Soc. Jpn. 1997, 70, 3117-3128
33. Fujii, N., Kakiuchi, F., Yamada, A., Chatani, N., and Murai, S. Bull. Chem. Soc. Jpn. 1998, 71, 285-298
34. Kakiuchi, F., Le Gendre, P., Yamada, A., and Ohtaki, H. Tetrahedron: Asymmetry 2000, 11, 2647-2651
35. Kakiuchi, F., Ohtaki, H., Sonoda, M., Chatani, N., and Murai, S. Chem. Lett. 2001, 918-919
36. Chatani, N., Asaumi, T., Yorimitsu, S., Ikeda, T., Kakiuchi, F., and Murai, S. J. Am. Chem. Soc. 2001, 123, 10935-10941
37. Kakiuchi, F. and Murai, S. Acc. Chem. Res. 2002, 35, 826-834
38. Lim, Y.-G., Kim, Y. H., and Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267-2268
39. Guo, H., Wang, G., Tapsak, M. A., and Weber, W. P. Macromolecules 1995, 28, 5686-5687
40. Trost, B. M., Imi, K., and Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371-5372
41. Harris, P. W. R. and Woodgate, P. D. J. Organomet. Chem. 1996, 506, 339-341
42. Lim, Y.-G., Kang, J.-B., and Kim, Y. H. Chem. Commun. 1996, 585-586
43. Grigg, R. and Savic, V. Tetrahedron Lett. 1997, 38, 5737-5740
44. Lu, P., Paulasaari, J. K., and Weber, W. P. Organometallics 1998, 17, 584-588
45. Lenges, C. P. and Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616-6623
46. Tan, K. L., Bergman, R. G., and Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685-2686
47. Thalji, R. K., Ahrendt, K. A., Bergman, R. G., and Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692-9693
48. DeBoef, B., Pastine, S. J., and Sames, D. J. Am. Chem. Soc. 2004, 126, 6556-6557
49. Lim, S.-G., Ahn, J.-A., and Jun, C.-H. Org. Lett. 2004, 6, 4687-4690
50. Martinez, R., Chevalier, R., Darses, S., and Genet, J.-P. Angew. Chem., Int. Ed. 2006, 45, 8232-8235
51. Lewis, J. C., Bergman, R. G., and Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332-5333
52. Hwang, S. J., Cho, S. H., and Chang, S. J. Am. Chem. Soc. 2008, 130, 16158-16159
53. Nakao, Y., Kashihara, N., Kanyiva, K. S., and Hiyama, T. J. Am. Chem. Soc. 2008, 130, 16170-16171
54. Kuninobu, Y., Nishina, Y., Okaguchi, K., Shouho, M., and Takai, K. Bull. Chem. Soc. Jpn. 2008, 81, 1393-1401
55. Kozhushkov, S., Yufit, D. S., and Ackermann, L. Org. Lett. 2008, 10, 3409-3412
56. Tsuchikama, K., Kasagawa, M., Hashimoto, Y.-K., Endo, K., and Shibata, T. J. Organomet. Chem. 2008, 693, 3939-3942
57. Martinez, R., Simon, M.-O., Chevalier, R., Pautigny, C., Genet, J.-P., and Darses, S. J. Am. Chem. Soc. 2009, 131, 7887-7895
58. Mukai, T., Hirano, K., Satoh, T., and Miura, M. J. Org. Chem. 2009, 74, 6410-6413
59. Nakao, Y., Idei, H., Kanyiva, K. S., and Hiyama, T. J. Am. Chem. Soc. 2009, 131, 15996-15997
60. Nakazono, S., Imazaki, Y., Yoo, H., Yang, J., Sasamori, T., Tokitoh, N., Cédric, T., Kageyama, H., Kim, D., Shinokubo, H., and Osuka, A. Chem.-Eur. J. 2009, 15, 7530-7533
61. Yi, C. S. and Lee, D. W. Organometallics 2009, 28, 4266-4268
62. Bartoszewicz, A. and Martín-Matute, B. Org. Lett. 2009, 11, 1749-1752
63. Simon, M.-O., Martinez, R., Genet, J.-P., and Darses, S. J. Org. Chem. 2010, 75, 208-210
64. Guari, Y., Sabo-Etienne, S., and Chaudret, B. J. Am. Chem. Soc. 1998, 120, 4228-4229
65. Guari, Y., Castellanos, A., Sabo-Etienne, S., and Chaudret, B. J. Mol. Catal. A: Chem. 2004, 212, 77-82
66. Busch, S. and Leitner, W. Adv. Synth. Catal. 2001, 343, 192-195
67. Busch, S. and Leitner, W. Chem. Commun. 1999, 2305-2306
68. Buskens, P., Giunta, D., and Leitner, W. Inorg. Chim. Acta 2004, 357, 1969-1974
69. Hong, P., Cho, B.-R., and Yamazaki, H. Chem. Lett. 1979, 8, 339-342
70. Hong, P., Cho, B.-R., and Yamazaki, H. Chem. Lett. 1980, 9, 507-510
71. Yamazaki, H. and Hong, P. J. Mol. Catal. 1983, 21, 133-150
72. Halbritter, G., Knoch, F., Wolski, A., and Kisch, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603-1605
73. Kakiuchi, F., Yamamoto, Y., Chatani, N., and Murai, S. Chem. Lett. 1995, 681-682
74. Dürr, U. and Kisch, H. Synlett 1997, 1335-1341
75. Londergan, T. M., You, Y., Thompson, M. E., and Weber, W. P. Macromolecules 1998, 31, 2784-2788
76. Satoh, T., Nishinaka, Y., Miura, M., and Nomura, M. Chem. Lett. 1999, 615-616
77. Harris, P. W. R., Rickard, C. E. F., and Woodgate, P. D. J. Organomet. Chem. 1999, 589, 168-179
78. Sakaguchi, S., Kubo, T., and Ishii, Y. Angew. Chem., Int. Ed. 2001, 40, 2534-2536
79. Lim, Y.-G., Lee, K.-H., Koo, B. T., and Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609-7612
80. Kakiuchi, K., Uetsuhara, T., Tanaka, Y., Chatani, N., and Murai, S. J. Mol. Catal. A 2002, 182-183, 511-514
81. Lim, S.-G., Lee, J. H., Moon, C. W., Hong, J.-B., and Jun, C.-H. Org. Lett. 2003, 5, 2759-2761
82. Tsukada, N., Mitsuboshi, T., Setoguchi, H., and Inoue, Y. J. Am. Chem. Soc. 2003, 125, 12102-12103
83. Kuninobu, Y., Kawata, A., and Takai, K. J. Am. Chem. Soc. 2005, 127, 13498-13499
84. Kuninobu, Y., Tokunaga, Y., Kawata, A., and Takai, K. J. Am. Chem. Soc. 2006, 128, 202-209
85. Ueura, K., Satoh, T., and Miura, M. Org. Lett. 2007, 9, 1407-1409
86. Ueura, K., Satoh, T., and Miura, M. J. Org. Chem. 2007, 72, 5362-5367
87. Tsukada, N., Murata, K., and Inoue, Y. Tetrahedron Lett. 2005, 46, 7515-7517
88. Nakao, Y., Yada, A., Ebata, S., and Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428-2429
89. Hong, P. and Yamazaki, H. Chem. Lett. 1979, 8, 1335-1336
90. Lin, Y., Ma, D., and Lu, X. Tetrahedron Lett. 1987, 28, 3249-3252
91. Kakiuchi, F., Sato, T., Yamauchi, M., Chatani, N., and Murai, S. Chem. Lett. 1999, 28, 19-20
92. Ueno, S, Chatani, N., and Kakiuchi, F. J. Org. Chem. 2007, 72, 3600-3602
93. Matsuura, Y., Tamura, M., Kochi, T., Sato, M., Chatani, N., and Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 9858-9859
94. Ueno, S., Kochi, T., Chatani, N., and Kakiuchi, F. Org. Lett. 2009, 11, 855-858
95. Moore, E. J., Pretzer, W. R., O'Connell, T. J., Harris, J., LaBounty, L., Chou, L., and Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888-5890
96. Chatani, N., Fukuyama, T., Kakiuchi, F., and Murai, S. J. Am. Chem. Soc. 1996, 118, 493-494
97. Chatani, N., Ie, Y., Kakiuchi, F., and Murai, S. J. Org. Chem. 1997, 62, 2604-2610
98. Chatani, N., Ishii, Y., Ie, Y., Kakiuchi, F., and Murai, S. J. Org. Chem. 1998, 63, 5129-5136
99. Chatani, N., Asaumi, T., Ikeda, T., Yorimitsu, S., Ishii, Y., Kakiuchi, F., and Murai, S. J. Am. Chem. Soc. 2000, 122, 12882-12883
100. Szewczyk, J. W., Zuckerman, R. L., Bergman, R. G., and Ellman, J. A. Angew. Chem., Int. Ed. 2001, 40, 216-219
101. Asaumi, T., Matsuo, T., Fukuyama, T., Ie, Y., Kakiuchi, F., and Chatani, N. J. Org. Chem. 2004, 69, 4433-4440
102. Imoto, S., Uemura, T., Kakiuchi, F., and Chatani, N. Synlett 2007, 170-172
103. Inoue, S., Shiota, H., and Fukumoto, Y. J. Am. Chem. Soc. 2009, 131, 6898-6899
104. Kakiuchi, F., Kan, S., Igi, K., Chatani, N., and Murai, S. J. Am. Chem. Soc. 2003, 125, 1698-1699
105. Kakiuchi, F., Matsuura, Y., Kan, S., and Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936-5945
106. Ueura, K., Satoh, T., and Miura, M. Org. Lett. 2005, 7, 2229-2231
107. Miyamura, S., Tsurugi, H., Satoh, T., and Miura, M. J. Organomet. Chem. 2008, 693, 2438-2442
108. Gustavson, W. A., Epstein, P. S., and Curtis, M. D. Organometallics 1982, 1, 884-885
109. Ishikawa, M., Sakamoto, H., Okazaki, S., and Naka, A. J. Organomet. Chem. 1992, 439, 19-21
110. Uchimaru, Y., El Sayed, A. M. M., and Tanaka, M. Organometallics 1993, 12, 2065-2069
111. Djurovich, P. I., Dolich, A. R., and Berry, D. H. J. Chem. Soc., Chem. Commun. 1994, 1897-1898
112. Ishikawa, M. and Naka, A. Synlett 1995, 794-802
113. Williams, N. A., Uchimaru, Y., and Tanaka, M. J. Chem. Soc., Chem. Commun. 1995, 1129-1130
114. Kakiuchi, F., Matsumoto, M., Sonoda, M., Fukuyama, T., Chatani, N., Murai, S., Furukawa, N., and Seki, Y. Chem. Lett. 2000, 750-751
115. Kakiuchi, F., Igi, K., Matsumoto, M., Chatani, N., and Murai, S. Chem. Lett. 2001, 422-423
116. Kakiuchi, F., Igi, K., Matsumoto, M., Hayamizu, T., Chatani, N., and Murai, S. Chem. Lett. 2002, 396-397
117. Kakiuchi, F., Matsumoto, M., Tsuchiya, K., Igi, K., Hayamizu, T., Chatani, N., and Murai, S. J. Organomet. Chem. 2003, 686, 134-144
118. Williams, N. A., Uchimaru, Y., and Tanaka, M. Dalton Trans. 2003, 236-243
119. Ishiyama, T., Sato, K., Nishio, Y., and Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 5346-5348
120. Tsukada, N. and Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6022-6023
121. Ishiyama, T., Sato, K., Nishio, Y., Saiki, T., and Miyaura, N. Chem. Commun. 2005, 5065-5067
122. Saiki, T., Nishio, Y., Ishiyama, T., and Miyaura, N. Organometallics 2006, 25, 6068-6073
123. Murata, M., Fukuyama, N., Wada, J.-I., Watanabe, S., and Masuda, Y. Chem. Lett. 2007, 36, 910-911
124. Waltz, K. M., He, X., Muhoro, C., and Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11357-11358
125. Waltz, K. M. and Hartwig, J. F. Science 1997, 277, 211-213
126. Chen, H., Schlecht, S., Semple, T. C., and Hartwig, J. F. Science 2000, 287, 1995-1997
127. Cho, J.-Y., Iverson, C. N., and Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868-12869
128. Cho, J.-Y., Tse, M. K., Holmes, D., Maleczka, R. E., Jr., and Smith, M. R., III. Science 2002, 295, 305-308
129. Ishiyama, T., Takagi, J., Ishida, K., and Miyaura, N. J. Am. Chem. Soc. 2002, 124, 390-391
130. Ishiyama, T., Takagi, J., Hartwig, J. F., and Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056-3058
131. Hartwig, J. F. In Activation and Functionalization of C-H Bonds; Goldberg, K. I. and Goldman, A. S., Eds.; ACS Symposium Series 885; American Chemical Society: Washington, DC, 2004; pp 136 - 154.
132. Hartwig, J. F. and Lawrence, J. D. In Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005; Vol. 2, pp 605 - 615.
133. Ishiyama, T. and Miyaura, N. Pure Appl. Chem. 2006, 78, 1369-1375
134. Matsubara, T., Koga, N., Musaev, D. G., and Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692-12693
135. Matsubara, T., Koga, N., Musaev, D. G., and Morokuma, K. Organometallics 2000, 19, 2318-2329
136. Hiraki, K., Ishimoto, T., and Kawano, H. Bull. Chem. Soc. Jpn. 2000, 73, 2099-2108
137. Jazzer, R. F. R., Mahon, M. F., and Whittlesey, M. K. Organometallics 2001, 20, 3745-3751
138. Drouin, S. D., Amoroso, D., Yap, G. P. A., and Fogg, D. E. Organometallics 2002, 21, 1042-1049
139. Appleton, T. G., Bennett, M. A., and Tomkins, I. B. J. Chem. Soc., Dalton Trans. 1976, 439-440
140. Cole-Hamilton, D. J. and Wilkinson, G. J. Chem. Soc., Dalton Trans. 1977, 797-804
141. Garrou, P. E. Chem. Rev. 1981, 81, 229-266
142. Mohr, F., Privér, S. H., Bhargava, S. K., and Bennett, M. A. Coord. Chem. Rev. 2006, 250, 1851-1888
143. Roper, W. R. and Wright, L. J. J. Organomet. Chem. 1982, 234, C5-C8
144. Darses and co-workers recently reported highly efficient C-H alkylation of aromatic ketones using an in situ-generated ruthenium catalyst. See ref 3t.
145. Kitamura, M., Tsukamoto, M., Bessho, Y., Yoshimura, M., Kobs, U., Widhalm, M., and Noyori, R. J. Am. Chem. Soc. 2002, 124, 6649-6667