Homogeneous CO hydrogenation: Ligand effects on the lewis acid-assisted reductive coupling of carbon monoxide

Organometallics

Volumn 29, Issue 20, 2010, Pages 4499-4516

  Miller, Alexander J M ^a   Labinger, Jay A ^a   Bercaw, John E ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID STRENGTHS; BONDED PRODUCTS; C-C BOND FORMING; CARBENES; CARBON ATOMS; CO HYDROGENATION; CO-GROUP; HYDRIDE TRANSFERS; LEWIS ACID; LIGAND EFFECT; REDUCTIVE COUPLINGS; RHENIUM CARBONYL COMPLEXES; STRUCTURE-FUNCTION STUDIES; WORKING MODELS;

ACIDS; BORON COMPOUNDS; CARBON MONOXIDE; CHLORINE COMPOUNDS; DYES; HYDRIDES; PERSONAL COMPUTERS; PLATINUM; RHENIUM; RHENIUM COMPOUNDS;

LIGANDS;

EID: 77958100538     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100638d     Document Type: Article

References (85)

1. Khodakov, A. Y.; Chu, W.; Fongarland, P. Chem. Rev. 2007, 107, 1692
2. Rofer-DePoorter, C. K. Chem. Rev. 1981, 81, 447
3. United Nations Development Program. World Energy Assessment Report: Energy and the Challenge of Sustainability; United Nations, New York, 2000.
4. Gladysz, J. A. Adv. Organomet. Chem. 1982, 20, 1
5. Herrmann, W. A. Angew. Chem., Int. Ed. 1982, 21, 117
6. Cutler, A. R.; Hanna, P. K.; Vites, J. C. Chem. Rev. 1988, 88, 1363
7. Wolczanski, P. T.; Bercaw, J. E. Acc. Chem. Res. 1980, 13, 121
8. Collman, J. P.; Winter, S. R. J. Am. Chem. Soc. 1973, 95, 4089
9. Casey, C. P.; Neumann, S. M. J. Am. Chem. Soc. 1976, 98, 5395
10. Tam, W.; Wong, W.-K.; Gladysz, J. A. J. Am. Chem. Soc. 1979, 101, 1589
11. Casey, C. P.; Andrews, M. A.; McAlister, D. R.; Rinz, J. E. J. Am. Chem. Soc. 1980, 102, 1927
12. Sweet, J. R.; Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 2811
13. Brown, S. L.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1986, 84
14. Manriquez, J. M.; McAlister, D. R.; Sanner, R. D.; Bercaw, J. E. J. Am. Chem. Soc. 1978, 100, 2716
15. Fagan, P. J.; Moloy, K. G.; Marks, T. J. J. Am. Chem. Soc. 1981, 103, 6959
16. Gambarotta, S.; Floriani, C.; Chiesivilla, A.; Guastini, C. J. Am. Chem. Soc. 1983, 105, 1690
17. Evans, W. J.; Grate, J. W.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 1671
18. Miller, R. L.; Toreki, R.; Lapointe, R. E.; Wolczanski, P. T.; Vanduyne, G. D.; Roe, D. C. J. Am. Chem. Soc. 1993, 115, 5570
19. Werkema, E. L.; Maron, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2007, 129, 2529
20. Shima, T.; Hou, Z. J. Am. Chem. Soc. 2006, 128, 8124
21. Dombek, B. D. Adv. Catal. 1983, 32, 325
22. Demitras, G. C.; Muetterties, E. L. J. Am. Chem. Soc. 1977, 99, 2796
23. Miller, A. J. M.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2008, 130, 11874
24. Elowe, P. R.; West, N. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2009, 28, 6218
25. Miller, A. J. M.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2010, 132, 3301
26. 2, as detailed in the Supporting Information.
27. Miedaner, A.; DuBois, D. L.; Curtis, C. J.; Haltiwanger, R. C. Organometallics 1993, 12, 299
28. Curtis, C. J.; Miedaner, A.; Ellis, W. W.; DuBois, D. L. J. Am. Chem. Soc. 2002, 124, 1918
29. DuBois, M. R.; DuBois, D. L. Chem. Soc. Rev. 2009, 38, 62
30. Crawford, E. J.; Bodnar, T. W.; Cutler, A. R. J. Am. Chem. Soc. 1986, 108, 6202
31. Yamamoto, H. Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000.
32. Butts, S. B.; Holt, E. M.; Strauss, S. H.; Alcock, N. W.; Stimson, R. E.; Shriver, D. F. J. Am. Chem. Soc. 1979, 101, 5864
33. Butts, S. B.; Strauss, S. H.; Holt, E. M.; Stimson, R. E.; Alcock, N. W.; Shriver, D. F. J. Am. Chem. Soc. 1980, 102, 5093
34. Labinger, J. A.; Miller, J. S. J. Am. Chem. Soc. 1982, 104, 6856
35. Grimmett, D. L.; Labinger, J. A.; Bonfiglio, J. N.; Masuo, S. T.; Shearin, E.; Miller, J. S. J. Am. Chem. Soc. 1982, 104, 6858
36. Labinger, J. A.; Bonfiglio, J. N.; Grimmett, D. L.; Masuo, S. T.; Shearin, E.; Miller, J. S. Organometallics 1983, 2, 733
37. Maitlis, P. M.; Zanotti, V. Chem. Commun. 2009, 1619
38. See Supporting Information for full details.
39. 2 in solution.
40. 13C chemical shift of Re-CHO. Solid-state structures appear to be intermediate between carbene and formyl.
41. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703
42. Rose, N. J.; Drago, R. S. J. Am. Chem. Soc. 1959, 81, 6138
43. Baldwin, S. M.; Bercaw, J. E.; Brintzinger, H. H. J. Am. Chem. Soc. 2008, 130, 17423
44. Narayanan, B. A.; Amatore, C. A.; Kochi, J. K. Organometallics 1984, 3, 802
45. Sumner, C. E.; Nelson, G. O. J. Am. Chem. Soc. 1984, 106, 432
46. Narayanan, B. A.; Amatore, C.; Kochi, J. K. Organometallics 1987, 6, 129
47. Elowe, P. R. Ph.D. Thesis, California Institute of Technology, Pasadena, CA, 2009.
48. 14) as an analytically pure white powder. See Supporting Information for full details.
49. Brown, H. C.; Hébert, N. C.; Snyder, C. H. J. Am. Chem. Soc. 1961, 83, 1001
50. Brown, H. C.; Snyder, C. H. J. Am. Chem. Soc. 1961, 83, 1002
51. Brown, H. C.; Verbrugge, C.; Snyder, C. H. J. Am. Chem. Soc. 1961, 83, 1001
52. Lambert, J. B.; Zhang, S.; Ciro, S. M. Organometallics 1994, 13, 2430
53. Ingham, W. L.; Coville, N. J. Organometallics 1992, 11, 2551
54. Fischbach, A.; Bazinet, P. R.; Waterman, R.; Tilley, T. D. Organometallics 2008, 27, 1135
55. Kubo, K.; Nakazawa, H.; Nakahara, S.; Yoshino, K.; Mizuta, T.; Miyoshi, K. Organometallics 2000, 19, 4932
56. Luan, L.; Brookhart, M.; Templeton, J. L. Organometallics 1992, 11, 1433
57. Garrou, P. E. Chem. Rev. 1981, 81, 229
58. Li, D. Y.; Keresztes, I.; Hopson, R.; Williard, P. G. Acc. Chem. Res. 2009, 42, 270
59. Macchioni, A.; Ciancaleoni, G.; Zuccaccia, C.; Zuccaccia, D. Chem. Soc. Rev. 2008, 37, 479
60. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520
61. Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880
62. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46
63. DuBois, D. L.; Blake, D. M.; Miedaner, A.; Curtis, C. J.; DuBois, M. R.; Franz, J. A.; Linehan, J. C. Organometallics 2006, 25, 4414
64. Miedaner, A.; Raebiger, J. W.; Curtis, C. J.; Miller, S. M.; DuBois, D. L. Organometallics 2004, 23, 2670
65. Lin, W. B.; Wilson, S. R.; Girolami, G. S. Inorg. Chem. 1997, 36, 2662
66. Crawford, E. J.; Lambert, C.; Menard, K. P.; Cutler, A. R. J. Am. Chem. Soc. 1985, 107, 3130
67. Lindner, E.; von Au, G. Angew. Chem., Int. Ed. 1980, 19, 824
68. The reactivity in THF is consistent with the initially formed carbene undergoing fast disproportionation chemistry, just as the Re analogue.
69. 3(CHO) with trialkylboranes, as the formyl shifts upfield with added borane.
70. The large size of Re and P in these rings is expected to favor smaller ring sizes than organic counterparts, which suggests that seven- and eight-membered rings are more destablized than organic systems.
71. One possibility for this kinetic discrepancy could be tighter ion pairing for the smaller anions, which may aid in the transfer of hydride between two cationic species.
72. Tam, W.; Lin, G.-Y.; Gladysz, J. A. Organometallics 1982, 1, 525
73. Gibson, D. H.; Owens, K.; Mandal, S. K.; Sattich, W. E.; Franco, J. O. Organometallics 1989, 8, 498
74. 3 generally resulted in much more hydride formation and were thus avoided. These reactions were sometimes accompanied by intense color changes consistent with reduction processes, which would labilize the CO ligands and lead to reactivity at Re itself.
75. Eaton, G. R. J. Chem. Educ. 1969, 46, 547
76. Mckinney, R. J.; Kaesz, H. D. J. Am. Chem. Soc. 1975, 97, 3066
77. Casey, C. P.; Scheck, D. M. J. Am. Chem. Soc. 1980, 102, 2723
78. Casey, C. P.; Jones, J. J. Am. Chem. Soc. 1980, 102, 6154
79. Warner, K. E.; Norton, J. R. Organometallics 1985, 4, 2150
80. Martin, B. D.; Warner, K. E.; Norton, J. R. J. Am. Chem. Soc. 1986, 108, 33
81. Casey, C. P.; Andrews, M. A.; McAlister, D. R. J. Am. Chem. Soc. 1979, 101, 3371
82. Berke, H.; Weiler, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 150
83. Lenhert, P. G.; Lukehart, C. M.; Sotiropoulos, P. D.; Srinivasan, K. Inorg. Chem. 1984, 23, 1807
84. Djukic, J. P.; Dotz, K. H.; Pfeffer, M.; De Cian, A.; Fischer, J. Inorg. Chem. 1998, 37, 3649
85. Padolik, L. L.; Gallucci, J. C.; Wojcicki, A. J. Am. Chem. Soc. 1993, 115, 9986