Selective C-H activation of haloalkanes using a rhodiumtrispyrazolylborate complex

Journal of the American Chemical Society

Volumn 131, Issue 30, 2009, Pages 10742-10752

  Vetter, Andrew J ^a   Rieth, Ryan D ^a   Brennessel, William W ^a   Jones, William D ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PRODUCTS; C-H ACTIVATION; C-H BOND CLEAVAGE; CHLOROALKANES; CHLOROMETHANE; CLEAVAGE PRODUCTS; CYCLIC SUBSTRATES; DIASTEREOMERIC; HALOALKANES; KINETIC STABILITY; METAL CENTERS; NO ACTIVATION; REDUCTIVE ELIMINATION;

ACTIVATION ANALYSIS; CHLORINE; DICHLOROMETHANE;

RHODIUM;

ALKANE DERIVATIVE; BORIC ACID; CHLORINE DERIVATIVE; CYCLOPENTANE; CYCLOPENTANE DERIVATIVE; DICHLOROMETHANE; HALOOLEFIN; METAL; METHYL CHLORIDE; NEOPENTYL CHLORIDE; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; DIASTEREOISOMER; ELIMINATION REACTION; HYDROGEN BOND; MOLECULAR STABILITY; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 68049086902     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9002316     Document Type: Article

References (86)

1. (a) Goldberg, K. I.; Goldman, A. S., Eds. Activation and Functionalization of C-H Bonds; American Chemical Society; Washington,DC, 2004.
2. (b) Murai, S., Ed. Topics in OrganometallicChemistry; Springer: New York, 1999; Vol. 3.
3. Earlyexamples of C-Hbond activation chemistry using Cp- and Cp*-based metal complexes: (a) Green, M. L. H.; Knowles, P. J. J. Chem. Soc D 1970, 1677.
4. (b) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 352.
5. (c) Hoyano, J. K.; Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 3723.
6. (d) Janowicz, A. H.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 3929.
7. (e) Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1984, 106, 1650.
8. "Pincer complexes"containing a rigid tridentate ligand are one example of a class ofcompounds being explored for use in intermolecular C-H andC-C bond cleavage reactions. For some examples of their utility,see: (a) Kanzelberger, M.; Singh, B.; Czerw, M.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 2000, 122, 11017.
9. (b) Harkins, S. B.; Peters, J. C. Organometallics 2002, 21, 1753.
10. (c) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
11. (d) Cohen, R.; Rybtchinski, B.; Gandelman, M.; Shimon, L. J. W.; Martin, J.M. L.; Milstein, D. Angew. Chem., Int. Ed. 2003, 42, 1949.
12. (e) Novak, F.; Speiser, B.; Mohammad, H. A. Y.; Mayer, H. A. Electrochim. Acta 2004, 49, 3841.
13. (f) Ben-Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390.
14. N-heterocyclic carbenes (NHCs)are currently being explored as ligands for metal complexes used inintermolecular C-H bond cleavage chemistry. Recent examplesinclude: (a) Muehlhofer, M.; Strassner, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1745.
15. (b) Corberan, R.; Sanau, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974.
16. (c) Fructos, M. R.; De Fremont, P.; Nolan, S. P.; Mar Dauiiaz-Requejo, M.; Perez, P. J. Organometallics 2006, 25, 2237.
17. (d) Burling, S.; Paine, B. M.; Nama, D.; Brown, V. S.; Mahon, M. F.; Prior, T. J.; Pregosin, P. S.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2007, 129, 1987.
18. Trofimenko, S. J. Scorpionates. TheCoordination Chemistrry of Polypyrazolylborate Ligands; Imperial College Press: London, 1999.
19. Examples of C-Hbond activation chemistry using Tp-based metal complexes: (a) Ghosh, C. K.; Graham, W. A. G. J. Am. Chem. Soc. 1987, 109, 4726.
20. b) Ghosh, C. K.; Graham, W. A. G. J. Am. Chem. Soc. 1989, 111, 375.
21. (c) Jones, W. D.; Duttweiler, R. P., Jr; Feher, F. J.; Hessell, E. T. New J. Chem. 1989, 13, 725.
22. (d) Jones, W. D.; Hessell, E. T. Inorg. Chem. 1991, 30, 778.
23. (e) Slugovc, C.; Padilla-Martínez, I.; Sirol, S.; Carmona, E. Coord. Chem. Rev. 2001, 213, 129.
24. (a) Hessell, E. T.; Jones, W. D. Organometallics 1992, 11, 1496.
25. (b) Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1992, 114, 6087.
26. (c) Jones, W. D.; Hessell, E. T. J. Am. Chem. Soc. 1993, 115, 554.
27. (d) Jones, W. D.; Wick, D. D. Organometallics 1999, 18, 495.
28. (e) Wick, D. D.; Northcutt, T. O.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 4484.
29. (f) Wick, D. D.; Reynolds, K. A.; Jones, W. D. J. Am. Chem. Soc. 1999, 121, 3974.
30. (g) Northcutt, T. O.; Wick, D. D.; Vetter, A. J.; Jones, W. D. J. Am. Chem. Soc. 2001, 123, 7257.
31. (h) Vetter, A. J.; Flaschenriem, C.; Jones, W. D. J. Am. Chem. Soc. 2005, 127, 12315.
32. (a) Fan, L.; Parkin, S.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 16772.
33. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
34. (c) Tellers, D. T.; Yung, C. M.; Arndtsen, B. A.; Adamson, D. R.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 1400.
35. (d) Fuchita, Y.; Utsunomiya, Y.; Yasutake, M. J. Chem. Soc., Dalton Trans. 2001, 30.
36. (e) Selmeczy, A. D.; Jones, W. D.; Partridge, M. G.; Perutz, R. N. Organometallics 1994, 13, 522.
37. (f) Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831.
38. For examples ofborylationof mono- and polysubstituted arenes from Smith, see: (a) Cho, J.-Y.; Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 2000, 122, 12868.
39. (b) Tse, M. K.; Cho, J.-Y.; Smith, M. R. Org. Lett. 2001, 3, 2831.
40. (c) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr; Smith, M. R. Science 2002, 295, 305.
41. (d) Chotana, G. A.; Rak, M. A.; Smith III, M. R. J. Am. Chem. Soc. 2005, 127, 10539.
42. For examples of borylationof mono- and polysubstituted arenes from Hartwig, see: (a) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
43. (b) Ishiyama, T.; Takagi, J.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 3056.
44. (c) Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. J. Chem. Soc. Chem. Commun. 2003, 2924.
45. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
46. For an example of substitutedarene borylation followed by oxidation to yield substituted phenols,see: Maleczka Jr., R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792.
47. Tzschucke, C. C.; Murphy, J. M.; Hartwig, J. F. Org. Lett. 2007, 9, 761.
48. (a) Ben-Ari, E.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 4714.
49. (b) Ben-Ari, E.; Cohen, R.; Gandelman, M.; Shimon, L. J. W.; Martin, J. M. L.; Milstein, D. Organometallics 2006, 25, 3190.
50. (a) Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. J. Organomet. Chem. 1995, 504, 151.
51. (b) Sonoda, M.; Kakiuchi, F; Chatani, N.; Murai, S Bull. Chem. Soc. Jpn. 1997, 70, 3117.
52. Tsang, J. Y. K.; Buschhaus, M. S. A.; Legzdins, P.; Patrick, B. O. Organometallics 2006, 25, 4215.
53. (a) Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 15334.
54. (b) Hartwig, J. F.; Cook, K. S.; Hapke, M.; Incarvito, C. D.; Fan, Y.; Webster, C. E.; Hall, M. B. J. Am. Chem. Soc. 2005, 127, 2538.
55. (c) Murphy, J. M.; Lawrence, J. D.; Kawamura, K.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 13684.
56. In aspecial issue dedicated to scorpionate ligands: Vetter, A. J.; Jones, W. D. Polyhedron 2004, 23, 413.
57. Mechanism and Theory in Organic Chemistry, 3rd ed.; Lowry, T. H., Richardson, K. S. , Eds.; Harper and Row: New York, 1987.
58. Grushin, V. V.; Alper, H. In Topics in OrganometallicChemistry; Murai, S., Ed.; Springer-Verlag: New York, 1999; Vol. 3, p 192.
59. Wick, D. D.; Jones, W. D. Inorg. Chem. 1997, 36, 2723.
60. For recent reports ofdichloromethane activation, see: (a) Tejel, C.; Ciriano, M. A.; Lopez, J. A.; Jimenez, S.; Bordonaba, M.; Oro, L. A Chem. - Eur. J. 2007, 13, 2044.
61. (b) Wright, J. A.; Danopoulos, A. A.; Motherwell, W. B.; Carroll, R. J.; Ellwood, S.; Sassmannshausen, J Eur. J. Inorg. Chem. 2006, 4857.
62. (c) Ito, J.; Miyakawa, T.; Nishiyama, H. Organometallics 2006, 25, 5216.
63. (d) Ho, J. H. H.; Black, D. S. C.; Messerle, B. A.; Clegg, J. K.; Turner, P. Organometallics 2006, 25, 5800.
64. (e) Burkill, H. A.; Vilar, R.; White, A. J. P. Inorg. Chim. Acta 2006, 359, 3709.
65. (a) Kunkely, H.; Vogler, A. Inorg. Chem. Commun. 2002, 5, 730.
66. (b) Plyusnin, V. F.; Grivin, V. P.; Larionov, S. V. Coord. Chem. Rev. 1997, 159, 121.
67. Teuma, E.; Malbosc, F.; Etienne, M.; Daran, J.-C.; Kalck, P. J. Organomet. Chem. 2004, 689, 1763.
68. 5)(H).
69. 3 (0.15). See Hansch, C.; Leo, A.; Taft, R. W Chem. Rev. 1991, 91, 165.
70. Vetter, A. J.; Rieth, R. D.; Jones, W. D. Proc. Nat. Acad. Sci. 2007, 104, 6957.
71. Cundari, T. R.; Vaddadi, S. Inorg. Chim. Acta 2004, 357, 2863.
72. (a) Albietz, P. J.; Cleary, B. P.; Paw, W.; Eisenberg, R. J. Am. Chem. Soc. 2001, 123, 12091.
73. (b) Butts, M. D.; Scott, B. L.; Kubas, G. J. J. Am. Chem. Soc. 1996, 118, 11831.
74. de Jong, G. T.; Bickelhaupt, F. M. J. Chem. Theory Comput. 2006, 2, 322.
75. Weissman, M.; Benson, S. W. J. Phys. Chem. 1983, 87, 243.
76. Clot, E.; Eisenstein, O.; Jones, W. D. Proc. Nat. Acad. Sci. 2007, 104, 6939.
77. (a) Garcia, J. J.; Jones, W. D. Organometallics 2000, 19, 5544.
78. (b) Garcia, J. G.; Brunkan, N. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 9547.
79. (c) Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627.
80. (d) Garcia, J. J.; Arevalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997.
81. (e) Atesin, T. A.; Li, T.; Brennessel, W. W.; Lachaize, S.; Garcia, J. J.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 7562.
82. (f) Atesin, T. A.; Li, T.; Lachaize, S.; Garcia, J. J.; Jones, W. D. Organometallics 2008, 27, 3811.
83. Armarego, W. L. F.; Perrin, D. D. Purification of LaboratoryChemicals; Butterworth: Boston, 1996.
84. 2 (X = Cl or Br).
85. Roberts, J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 2509.
86. Hazari, S. K. S.; Dhar, D. J. Bang. Acad. Sci. 1992, 16, 241.