Synthesis and structure of intermediates in copper-catalyzed alkylation of diphenylphosphine

Inorganic Chemistry

Volumn 49, Issue 17, 2010, Pages 7650-7662

  Cain, Matthew F ^a   Hughes, Russell P ^a   Glueck, David S ^a   Golen, James A ^b   Moore, Curtis E ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956224855     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic100816u     Document Type: Article

References (85)

1. Scriban, C. and Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788-2789
2. Scriban, C., Glueck, D. S., Golen, J. A., and Rheingold, A. L. Organometallics 2007, 26, 1788-1800
3. (Addition/Correction: Scriban, C., Glueck, D. S., Golen, J. A., and Rheingold, A. L. Organometallics 2007, 26, 5124)
4. Glueck, D. S. Synlett 2007, 2627-2634
5. Glueck, D. S. Coord. Chem. Rev. 2008, 252, 2171-2179
6. Anderson, B. J., Glueck, D. S., DiPasquale, A. G., and Rheingold, A. L. Organometallics 2008, 27, 4992-5001
7. (Addition/Correction: Anderson, B. J., Glueck, D. S., DiPasquale, A. G., and Rheingold, A. L. Organometallics 2009, 28, 386)
8. Anderson, B. J., Guino-o, M. A., Glueck, D. S., Golen, J. A., DiPasquale, A. G., Liable-Sands, L. M., and Rheingold, A. L. Org. Lett. 2008, 10, 4425-4428
9. Chapp, T. W., Glueck, D. S., Golen, J. A., Moore, C. E., and Rheingold, A. L. Organometallics 2010, 29, 378-388
10. Chapp, T. W., Schoenfeld, A. J., and Glueck, D. S. Organometallics 2010, 29, 2465-2473
11. Chan, V. S., Stewart, I. C., Bergman, R. G., and Toste, F. D. J. Am. Chem. Soc. 2006, 128, 2786-2787
12. Chan, V. S., Chiu, M., Bergman, R. G., and Toste, F. D. J. Am. Chem. Soc. 2009, 131, 6021-6032
13. Glueck, D. S. Dalton Trans. 2008, 5276-5286
14. Rogers, J. R., Wagner, T. P. S., and Marynick, D. S. Inorg. Chem. 1994, 33, 3104-3110
15. Glueck, D. S. Chem.=Eur. J. 2008, 14, 7108-7117
16. Meyer, C., Grützmacher, H., and Pritzkow, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2471-2473
17. Meyer, C., Scherer, M., Schönberg, H., Rüegger, H., Loss, S., Gramlich, V., and Grützmacher, H. Dalton Trans. 2006, 137-148
18. Langford, C. H. and Gray, H. B. Ligand Substitution Processes; W. A. Benjamin: New York, 1966.
19. Scriban, C., Wicht, D. K., Glueck, D. S., Zakharov, L. N., Golen, J. A., and Rheingold, A. L. Organometallics 2006, 25, 3370-3378
20. For the structures of related Cu(XantPhos) complexes, see: Kaltzoglou, A., Fassler, T. F., and Aslanidis, P. J. Coord. Chem. 2008, 61, 1774-1781
21. Huang, J., Chan, J., Chen, Y., Borths, C. J., Baucom, K. D., Larsen, R. D., and Faul, M. M. J. Am. Chem. Soc. 2010, 132, 3674-3675
22. 2.
23. Gandhi, B. A., Green, O., and Burstyn, J. N. Inorg. Chem. 2007, 46, 3816-3825
24. Braussaud, N., Ruther, T., Cavell, K. J., Skelton, B. W., and White, A. H. Synthesis 2001, 626-632
25. Burck, S., van Assema, S. G. A., Lastdrager, B., Slootweg, J. C., Ehlers, A. W., Otero, J. M., Dacunha-Marinho, B., Llamas-Saiz, A. L., Mar, O., van Raaij, M. J., and Lammertsma, K. Chem.=Eur. J. 2009, 15, 8134-8145
26. Buhro, W. E., Georgiou, S., Hutchinson, J. P., and Gladysz, J. A. J. Am. Chem. Soc. 1985, 107, 3346-3348
27. Buhro, W. E., Zwick, B. D., Georgiou, S., Hutchinson, J. P., and Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 2427-2439
28. Heydenreich, F., Mollbach, A., Wilke, G., Dreeskamp, H., Hoffmann, E. G., Schroth, G., Seevogel, K., and Stempfle, W. Isr. J. Chem. 1972, 10, 293-319
29. Millauer, H. and Brungs, P. U.S. 5808163, 1998.
30. Berens, U. EP 1582527A1, 2005.
31. Seyferth, D., Wood, T. G., and Henderson, R. S. J. Organomet. Chem. 1987, 336, 163-182
32. Gillespie, D. G. and Walker, B. J. Tetrahedron Lett. 1975, 16, 4709-4710
33. Gillespie, D. G., Walker, B. J., Stevens, D., and McAuliffe, C. A. J. Chem. Soc., Perkin Trans. 1 1983, 1697-1703
34. Gillespie, D. G. and Walker, B. J. J. Chem. Soc., Perkin Trans. 1 1983, 1689-1695
35. Hewertson, W., Taylor, I. C., and Trippett, S. J. Chem. Soc. C 1970, 1835-1839
36. Hewertson, W. and Taylor, I. C. J. Chem. Soc. D 1970, 119-120
37. Issleib, K. and Muller, D.-W. Chem. Ber. 1959, 92, 3175-3182
38. Issleib, K. and Döll, G. Chem. Ber. 1961, 94, 2664-2669
39. Issleib, K. and Döll, G. Chem. Ber. 1963, 96, 1544-1550
40. Kourkine, I. V., Maslennikov, S. V., Ditchfield, R., Glueck, D. S., Yap, G. P. A., Liable-Sands, L. M., and Rheingold, A. L. Inorg. Chem. 1996, 35, 6708-6716
41. Black, J. R., Levason, W., Spicer, M. D., and Webster, M. J. Chem. Soc., Dalton Trans. 1993, 3129-3136
42. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122
43. Tye, J. W., Weng, Z., Giri, R., and Hartwig, J. F. Angew. Chem., Int. Ed. 2010, 49, 2185-2189
44. Tye, J. W., Weng, Z., Johns, A. M., Incarvito, C. D., and Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 9971-9983
45. Yin, Q. and Gan, X. Acta Crystallogr. 2010, E66, m369
46. For anionic terminal phosphido copper complexes, see: Cowley, A. H., Giolando, D. M., Jones, R. A., Nunn, C. M., and Power, J. M. J. Chem. Soc., Chem. Commun. 1988, 208-209
47. Martin, S. F., Fishpaugh, J. R., Power, J. M., Giolando, D. M., Jones, R. A., Nunn, C. M., and Cowley, A. H. J. Am. Chem. Soc. 1988, 110, 7226-7228
48. 2) was proposed on the basis of ebullioscopic molecular weight measurements: Van Koten, G., Noltes, J. G., and Spek, A. L. J. Organomet. Chem. 1978, 159, 441-463
49. Greiser, T. and Weiss, E. Chem. Ber. 1978, 111, 516-522
50. 31P NMR spectroscopy: Lemmen, T. H., Goeden, G. V., Huffman, J. C., Geerst, R. L., and Caulton, K. G. Inorg. Chem. 1990, 29, 3680-3685
51. Deeming, A. J., Doherty, S., Marshall, J. E., Powell, J. L., and Senior, A. M. J. Chem. Soc., Dalton Trans. 1993, 1093-1100
52. Zhuravel, M. A., Glueck, D. S., Zakharov, L. N., and Rheingold, A. L. Organometallics 2002, 21, 3208-3214
53. Bonnet, G., Kubicki, M. M., Moise, C., Lazzaroni, R., Salvadori, P., and Vitulli, G. Organometallics 1992, 11, 964-967
54. Reference 16a.
55. Mastrorilli, P. Eur. J. Inorg. Chem. 2008, 4835-4850
56. Eichenseher, S., Delacroix, O., Kromm, K., and Gladysz, J. A. Organometallics 2005, 24, 245-255
57. Caulton, K. G. New J. Chem. 1994, 18, 25-41
58. Holland, P. L., Andersen, R. A., and Bergman, R. G. Comments Inorg. Chem. 1999, 21, 115-129
59. Goj, L. A., Blue, E. D., Delp, S. A., Gunnoe, T. B., Cundari, T. R., Pierpont, A. W., Petersen, J. L., and Boyle, P. D. Inorg. Chem. 2006, 45, 9032-9045
60. 2, respectively, were observed.
61. Gunnoe, T. B. Eur. J. Inorg. Chem. 2007, 1185-1203
62. Jones, G. O., Liu, P., Houk, K. N., and Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205-6213
63. References 21b, 21c.
64. Gelman, D., Jiang, L., and Buchwald, S. L. Org. Lett. 2003, 5, 2315-2318
65. Van Allen, D. and Venkataraman, D. J. Org. Chem. 2003, 68, 4590-4593
66. Tani, K., Behenna, D. C., McFadden, R. M., and Stoltz, B. M. Org. Lett. 2007, 9, 2529-2531
67. Huang, C., Tang, X., Fu, H., Jiang, Y., and Zhao, Y. J. Org. Chem. 2006, 71, 5020-5022
68. Burk, M. J. and Harlow, R. L. Angew. Chem., Int. Ed. 1990, 29, 1462-1464
69. Burk, M. J., Feaster, J. E., and Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569-592
70. Ward, T. R., Venanzi, L. M., Albinati, A., Lianza, F., Gerfin, T., Gramlich, V., and Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983-988
71. Pangborn, A. B., Giardello, M. A., Grubbs, R. H., Rosen, R. K., and Timmers, F. J. Organometallics 1996, 15, 1518-1520
72. Kubas, G. J. Inorg. Synth. 1990, 28, 68-70
73. Pet, M. A., Cain, M. F., Hughes, R. P., Glueck, D. S., Golen, J. A., and Rheingold, A. L. J. Organomet. Chem. 2009, 694, 2279-2289
74. Goodwin, N. J., Henderson, W., and Nicholson, B. K. Chem. Commun. 1997, 31-32
75. Brauer, D. J., Bitterer, F., Dorrenbach, F., Hessler, G., Stelzer, O., Kruger, C., and Lutz, F. Z. Naturforsch. B 1996, 51, 1183-1196
76. Brookhart, M., Grant, B., and Volpe, A. F., Jr. Organometallics 1992, 11, 3920-3922
77. Irvine, D. J., Glidewell, C., Cole-Hamilton, D. J., Barnes, J. C., and Howie, A. J. Chem. Soc., Dalton Trans. 1991, 1765-1772
78. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1988, 37, 785-789
79. Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
80. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
81. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
82. Dunning, T. H. and Hay, P. J. In Modern Theoretical Chemistry, Vol. 4: Applications of Electronic Structure Theory.; Schaefer, H. F., III, Ed.; Plenum: New York, 1977.
83. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
84. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
85. Wadt, W. R. and Hay, P. J. J. Chem. Phys. 1985, 82, 284-298