Experimental and computational study of steric and electronic effects on the coordination of bulky, water-soluble alkylphosphines to palladium under reducing conditions: Correlation to catalytic activity

Organometallics

Volumn 24, Issue 5, 2005, Pages 962-971

  DeVasher, Rebecca B ^a   Spruell, Jason M ^a   Dixon, David A ^a   Broker, Grant A ^a   Griffin, Scott T ^a   Rogers, Robin D ^a   Shaughnessy, Kevin H ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CATALYTIC ACTIVITY; COORDINATION CHEMISTRY; LIGANDS;

CATALYSIS; CHEMICAL BONDS; PALLADIUM COMPOUNDS; PARAMETER ESTIMATION; SOLUBILITY; SUBSTRATES; THERMAL EFFECTS;

ORGANOMETALLICS;

EID: 14844328047     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049241w     Document Type: Article

References (80)

1. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
2. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
4. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
5. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
6. Negishi, E.-i.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
7. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
8. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
9. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
10. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
11. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
12. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
13. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
14. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731.
15. Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
16. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
17. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
18. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
19. Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678.
20. Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4641-4642.
21. You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003-8007.
22. Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153-4155.
23. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
24. Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Drosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363-1365.
25. Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
26. Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031-3033.
27. Navarro, O.; Kaur, N.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173-3180.
28. Bedford, R. B.; Hazelwood, S. L.; Limmert, M. E.; Albisson, D. A.; Draper, S. M.; Scully, P. N.; Coles, S. J.; Hursthouse, M. B. Chem. Eur. J. 2003, 9, 3216-3227.
29. Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797-6803.
30. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232-1233.
31. Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 1533-1541.
32. Andreu, M. G.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475-2476.
33. Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
34. Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346-9347.
35. Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184-1194.
36. Genêt, J. P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317.
37. Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed., John Wiley & Sons: New York, 2002; Vol. 2, pp 2957-3006.
38. Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
39. Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
40. Genêt, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443-1446.
41. Amatore, C.; Blart, E.; Genêt, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829-6839.
42. Paetzold, E.; Oehme, G. J. Mol. Catal. A: Chem. 2000, 152, 69-76.
43. Beller, M.; Krauter, J. G. E.; Zapf, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 772-774.
44. Hessler, A.; Stelzer, O.; Dibowski, H.; Worm, K.; Schmidtchen, F. P. J. Org. Chem. 1997, 62, 2362-2369.
45. Villemin, D.; Nechab, B. J. Chem. Res., Synop. 2000, 429-431.
46. Kolodziuk, R.; Penciu, A.; Tollabi, M.; Framery, E.; Goux-Henry, C.; Iourtchenko, A.; Sinou, D. J. Organomet. Chem. 2003, 687, 384-391.
47. Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7551-7554.
48. Wolf, C.; Lerebours, R. Org. Lett. 2004, 6, 1147-1150.
49. Nishimura, M.; Ueda, M.; Miyaura, N. Tetrahedron 2002, 58, 5779-5787.
50. Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317-4325.
51. Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757-2759.
52. DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919-7927.
53. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
54. Taverner, B. C. J. Comput. Chem. 1996, 17, 1612-1623.
55. Taverner, B. C., STERIC, 1.11, http://www.ccl.net/cca/software/SOURCES/C/ steric/index.shtml, 1995.
56. Bartik, T.; Himmler, T. J. Organomet. Chem. 1985, 293, 343-351.
57. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2953-2956.
58. Zhan, C.-G.; Nichols, J. A.; Dixon, D. A. J. Phys. Chem. A 2003, 107, 4184-4195.
59. Garza, J.; Vargas, R.; Nichols, J. A.; Dixon, D. A. J. Chem. Phys. 2001, 114, 639-661.
60. Perdew, J. P. Phys. Rev. B 1986, 33, 33-35.
61. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
62. Jenkins, J. M.; Shaw, B. L. Proc. Chem. Soc. 1963, 279.
63. See the Supporting Information for copies of the NMR spectra of this complex.
64. Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254-278.
65. Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
66. The relative catalytic activity of these systems has been based on product yields measured at short reaction times.
67. Sheldrick, G. M. SHELXTL, Version 6.14; Brüker Advanced X-Ray Solutions, Inc., 2000.
68. Sheldrick, G. M. Program for Semiempirical Absorption Correlation of Area Detector Data; University of Göttingen: Germany, 1996.
69. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630-6636.
70. Christe, K. O.; Dixon, D. A.; Mack, H. G.; Oberhammer, H.; Pagelot, A.; Sanders, J. C. P.; Schrobilgen, G. J. J. Am. Chem. Soc. 1993, 115, 11279-11284.
71. Casteel, W. J., Jr.; Dixon, D. A.; Mercier, H. P. A.; Schrobilgen, G. J. Inorg. Chem. 1996, 35, 4310-4322.
72. Casteel, W. J., Jr.; Dixon, D. A.; LeBlond, N.; Mercier, H. P. A.; Schrobilgen, G. J. Inorg. Chem. 1998, 37, 340-353.
73. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
74. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
75. Küchle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994, 100, 7536-7542, and references therein; http://www.theochem.uni-stuttgart.de/ pseudopotentials/.
76. Chen, H.; Krasowski, M.; Fitzgerald, G. J. Chem. Phys. 1993, 98, 8710-8717.
77. Vosko, S. J.; Wilk, L.; Nusair, W. Can. J. Phys. 1980, 58, 1200.
78. Andzelm, J.; Wimmer, E.; Salahub, D. R. In The Challenge of d and f Electrons: Theory and Computation; Salahub, D. R., Zerner, M. C., Eds.; ACS Symposium Series, No. 394, American Chemical Society: Washington, D.C., 1989; p 228.
79. Andzelm, J. In Density Functional Theory in Chemistry; Labauowski, J., Andzelm, J., Eds., Springer-Verlag: New York, 1991; p 155.
80. Andzelm, J.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280-1303.