Rate-limiting step of the Rh-catalyzed carboacylation of alkenes: C-C bond activation or migratory insertion?

Journal of the American Chemical Society

Volumn 134, Issue 1, 2012, Pages 715-722

  Lutz, J Patrick ^a   Rathbun, Colin M ^a   Stevenson, Susan M ^a   Powell, Breanna M ^a   Boman, Timothy S ^a   Baxter, Casey E ^a   Zona, John M ^a   Johnson, Jeffrey B ^a  

^a HOPE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE INSERTION; C-C BOND ACTIVATION; CARBOACYLATION; CARBON-CARBON BOND; CARBON-CARBON SINGLE BONDS; ELEMENTARY STEPS; FUNCTIONALIZATIONS; KINETIC ISOTOPE EFFECTS; MIGRATORY INSERTION; RATE LAWS; RATE LIMITING; RATE-LIMITING STEPS; RELATIVE ENERGIES; RHODIUM-CATALYZED;

ACTIVATION ANALYSIS; CARBON; CATALYSIS; CATALYSTS; ISOTOPES; KETONES; RHODIUM; RHODIUM COMPOUNDS; SUBSTRATES;

OLEFINS;

ALKENE DERIVATIVE; CARBON; ISOTOPE; KETONE; RHODIUM;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND;

EID: 84862917922     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210307s     Document Type: Article

References (96)

1. de Meijere, A.; Diederich, F. Metal-catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH: Weinheim, 2004.
2. Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; p 97.
3. Crabtree, R. H. Chem. Rev. 1985, 85, 245
4. Jones, W. D. Nature 1993, 364, 676
5. Schnuerch, M.; Dastbaravardeh, N.; Ghobrial, M.; Mrozek, B.; Mihovilovic, M. D. Curr. Org. Chem. 2011, 15, 2694
6. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
7. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem Soc. Rev. 2009, 38, 3242
8. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem, Int. Ed. 2009, 48, 5094
9. Crabtree, R. H. Dalton Trans. 2003, 3985
10. Crabtree, R. H. J. Chem. Soc., Dalton Trans. 2001, 2437
11. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1699
12. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154
13. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
14. Neĉas, D.; Kotora, M. Curr. Org. Chem. 2007, 11, 1566
15. Murakami, M.; Makino, M.; Ashida, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 2006, 79, 1315
16. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610
17. Hirata, Y.; Yada, A.; Morita, E.; Nakao, Y.; Hiyama, T.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2010, 132, 10070
18. Nakao, Y.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2010, 130, 10024
19. Najara, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452
20. Nakao, T.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874
21. Watson, M. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 12594
22. Ysaui, Y.; Kamisaki, H.; Takemoto, Y. Org. Lett. 2008, 10, 3303
23. Tobisu, M.; Kita, Y.; Ano, Y.; Chantani, N. J. Am. Chem. Soc. 2008, 130, 15982
24. Nishihara, Y.; Inoue, Y.; Itazaki, M.; Takagi, K. Org. Lett. 2005, 7, 2639
25. Penney, J. M.; Miller, J. M. Tetrahedron Lett. 2004, 45, 4989
26. Grenning, A. J.; Tunge, J. A. J. Am. Chem. Soc. 2011, 133, 14785
27. Han, C.; Kim, E. H.; Colby, D. A. J. Am. Chem. Soc. 2011, 133, 5802
28. Deb, I.; Seidel, D. Tetrahedron Lett. 2010, 51, 2945
29. Biswas, S.; Maiti, S.; Jana, U. Eur. J. Org. Chem. 2010, 2861
30. He, C.; Guo, S.; Huang, L.; Lei, A. J. Am. Chem. Soc. 2010, 132, 8273
31. Wei, Y.; Lui, J.; Lin, S.; Ding, H.; Liang, F.; Zhao, B. Org. Lett. 2010, 12, 4220
32. Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 11368
33. Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2009, 82, 778
34. Turský, M.; Neĉas, D.; Drabina, P.; Sedlák, M.; Kotora, M. Organometallics 2006, 25, 901
35. Nilsson, Y. I. M.; Andersson, P. G.; Bäckvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609
36. Neĉas, D.; Turský, M.; Kotora, M. J. Am. Chem. Soc. 2004, 126, 10222
37. Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T.-a. J. Am. Chem. Soc. 1998, 120, 5587
38. Oh, C. H.; Jung, S. H.; Bang, S. Y.; Park, D. I. Org. Lett. 2002, 4, 3325
39. Takada, Y.; Hayashi, S.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 2515
40. Satoh, T.; Jones, W. D. Organometallics 2001, 20, 2916
41. Müller, C.; Lachicotte, R. J.; Jones, W. D. Organometallics 2002, 21, 1975
42. Kondo, T.; Kaneko, Y.; Taguchi, Y.; Nakamura, A.; Okada, T.; Shiotsuki, M.; Ura, Y.; Wada, K.; Misudo, T. J. Am. Chem. Soc. 2002, 124, 6824
43. Ashida, S.; Murakami, M. Bull. Chem. Soc. Jpn. 2008, 81, 885
44. Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem.-Eur. J. 2002, 8, 2422
45. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
46. Salem, H.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. Organometallics 2006, 25, 2292
47. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870 and references therein.
48. Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340
49. Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Org. Lett. 2006, 8, 3379
50. Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407
51. Terao, Y.; Wakui, H.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236
52. Terao, Y.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2004, 69, 6942
53. Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862
54. Seiser, T.; Roth, O. A.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 6320
55. Shigeno, M.; Yamamoto, T.; Murakami, M. Chem.-Eur. J. 2009, 15, 12929
56. 2 extrusion, see: Chiba, S.; Xu, Y.-J.; Wang, Y.-F. J. Am. Chem. Soc. 2009, 131, 12886
57. Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244
58. Nishimura, T.; Katoh, T.; Takatsu, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14158
59. For reactions will alkynes, see: Schaub, T.; Backes, M.; Radius, U. Organometallics 2006, 25, 4196
60. Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412
61. Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Angew. Chem., Int. Ed. 2009, 48, 6121
62. Iverson, C. N.; Jones, W. D. Organometallics 2001, 20, 5745
63. Murakami, M.; Itahashi, T.; Ito, Y. J. Am. Chem. Soc. 2002, 124, 13976
64. Wender, P. A.; Correa, A. G.; Sator, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815
65. Yamamoto, Y.; Kuwabara, S.; Hayashi, H.; Nishiyama, H. Adv. Synth. Catal. 2006, 348, 2493
66. Crépin, D.; Dawick, J.; Aïssa, C. Angew. Chem., Int. Ed. 2010, 49, 620
67. Nishimura, T.; Matsumura, S.; Maeda, Y.; Uemura, S. Chem. Commun. 2002, 50
68. Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Org. Lett. 2006, 8, 3379
69. Matsuda, T.; Shigeno, M.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 12086
70. Sieser, T.; Cramer, N. Angew. Chem., Int. Ed. 2006, 45, 3957
71. Trost, B. M.; Zie, J. J. Am. Chem. Soc. 2008, 130, 6231 and ref 5e.
72. Rathbun, C. M.; Johnson, J. B. J. Am. Chem. Soc. 2011, 133, 2031
73. Ateşin, T. A.; Li, T.; Lachaize, S.; García, J. J.; Jones, W. D. Organometallics 2008, 27, 3811
74. Li, T.; García, J. J.; Brennessel, W. W.; Jones, W. D. Organometallics 2010, 29, 2430
75. Evans, M. E.; Li, T.; Jones, W. D. J. Am. Chem. Soc. 2010, 132, 16278
76. Obenhuber, A.; Ruhland, K. Organometallics 2011, 30, 4039
77. Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1984, 106, 3054
78. Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679
79. Singleton, D. A; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357
80. Frantz, D. E.; Singleton, D. A.; Snyder, J. P. J. Am. Chem. Soc. 1997, 119, 3383
81. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley-Interscience: New York, 1979.
82. Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031
83. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704
84. Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876
85. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175
86. Johnson, J. B.; Bercot, E. A.; Rowley, J. M.; Coates, G. W.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 2718
87. Pfretzschner, T.; Kleeman, L.; Janza, B.; Harms, K.; Schrader, T. Chem.-Eur. J. 2004, 10, 6048
88. C-H bond formation: Halpern, J. Asymmetric Synthesis; Academic Press: New York, 1983; Vol 5, p 48.
89. C-S bond formation: Moreau, X.; Campagne, J. M.; Meyer, G.; Jutand, A. Eur. J. Org. Chem. 2005, 3749
90. Hanley, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 15661
91. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840
92. Gómex-Gallego, M.; Sierra, M. A. Chem. Rev. 2011, 111, 4857
93. Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15258
94. Denmark, S. E.; Bui, T. J. Org. Chem. 2005, 70, 10393
95. Ŝvenda, J.; Evans, A. G. Org. Lett. 2009, 11, 2437
96. Edwards, D. R.; Montoya-Peleaz; Crudden, C. M. Org. Lett. 2007, 9, 5481