Rhenium-containing phosphorus donor ligands for palladium-catalyzed suzuki cross-coupling reactions: A new strategy for high-activity systems

Organometallics

Volumn 24, Issue 2, 2005, Pages 245-255

  Eichenseher, Sandra ^a   Delacroix, Olivier ^a,b   Kromm, Klemenz ^a,c   Hampel, Frank ^a   Gladysz, J A ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b 6 Bd du Maréchal Juin   (France)

^c Dynamit Nobel   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHROMATOGRAPHIC ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; ELECTRONIC PROPERTIES; HYDROGENATION; ORGANIC ACIDS; ORGANIC SOLVENTS; RHENIUM COMPOUNDS; SPECTROSCOPIC ANALYSIS;

BOND ANGLES; HIGH ACTIVITY SYSTEMS; SCOUTING REACTIONS; SPECTATOR METALS; SUZUKI CROSS COUPLING REACTIONS;

ORGANOMETALLICS;

EID: 12844288928     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0492956     Document Type: Article

References (74)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
3. (c) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
4. (d) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
5. (e) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201; Angew. Chem. 2004, 116, 2251.
6. (e) Miura, M. Angew. Chem., Int. Ed. 2004, 43, 2201; Angew. Chem. 2004, 116, 2251.
7. (a) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
8. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871; Angew. Chem. 2004, 116, 1907.
9. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871; Angew. Chem. 2004, 116, 1907.
10. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
11. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408.
12. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
13. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
14. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
15. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
16. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
17. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
18. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
19. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
20. This literature is enormous, and only approaches involving bulky and/or electron-rich phosphorus donor ligands are cited herein. In addition to refs 2 and 3, see: (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153; Angew. Chem. 2000, 112, 4315. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woolins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643, and earlier work cited therein. (d) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (e) Verkade, J. G.; Kisanga, P. B. Aldrichim. Acta 2004, 37, 3. (f) Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38. (g) Khanapure, S. P.; Garvey, D. S. Tetrahedron Lett. 2004, 45, 5283. (h) an der Heiden, M.; Plenio, H. Chem. Eur. J. 2004, 10, 1789.
21. Valentine, D. H., Jr.; Hillhouse, J. H. Synthesis 2003, 2437.
22. Minireview: Delacroix, O.; Gladysz, J. A. Chem. Commun. 2003, 665.
23. Buhro, W. E.; Zwick, B. D.; Georgiou, S.; Hutchinson, J. P.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 2427.
24. (a) Giner Planas, J.; Gladysz, J. A. Inorg. Chem. 2002, 41, 6947.
25. (b) Giner Planas, J.; Hampel, F.; Gladysz, J. A. Chem. Eur. J. 2005, 11, in press.
26. Dewey, M. A.; Knight, D. A.; Arif, A.; Gladysz, J. A. Chem. Ber. 1992, 125, 815.
27. McCormick, F. B.; Gleason, W. B.; Zhao, X.; Heah, P. C.; Gladysz, J. A. Organometallics 1986, 5, 1778.
28. (a) Fulton, J. R.; Sklenak, S.; Bouwkamp, M. W.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 4722.
29. (b) Holland, A. W.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 14684.
30. (c) Fox, D. J.; Bergman, R. G. Organometallics 2004, 23, 1656.
31. Conner, D.; Jayaprakash, K. N.; Gunnoe, T. B.; Boyle, P. D. Inorg. Chem. 2002, 41, 3042.
32. Caulton, K. G. New J. Chem. 1994, 18, 25.
33. For other possible contributing factors, see: Holland, P. L.; Andersen, R. A.; Bergman, R. G. Comments Inorg. Chem. 1999, 21, 115.
34. Zwick, B. D.; Dewey, M. A.; Knight, D. A.; Buhro, W. E.; Arif, A. M.; Gladysz, J. A. Organometallics 1992, 11, 2673.
35. O'Connor, A. R.; Nataro, C. Organometallics 2004, 23, 615.
36. Eichenseher, S.; Kromm, K.; Delacroix, O.; Gladysz, J. A. Chem. Commun. 2002, 1046.
37. (a) Kromm, K.; Zwick, B. D.; Meyer, O.; Hampel, F.; Gladysz, J. A. Chem. Eur. J. 2001, 7, 2015.
38. (b) Kromm, K.; Hampel, F.; Gladysz, J. A. Organometallics 2002, 21, 4264.
39. (c) Kromm, K.; Osburn, P. L.; Gladysz, J. A. Organometallics 2002, 21, 4275.
40. Agbossou, F.; O'Connor, E. J.; Garner, C. M.; Quirós Méndez, N.; Fernández, J. M.; Patton, A. T.; Ramsden, J. A.; Gladysz, J. A. Inorg. Synth. 1992, 29, 211.
41. To help consolidate a fragmented literature, updated syntheses and characterization of the previously reported rhenium complexes in Scheme 1 (and alternative salts for some cations) are provided in the Supporting Information.
42. (a) Heah, P. C.; Patton, A. T.; Gladysz, J. A. J. Am. Chem. Soc. 1986, 108, 1185.
43. (b) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729.
44. Casey, C. P.; Czerwinski, C. J.; Hayashi, R. K. Organometallics 1996, 15, 4362, and references therein.
45. (a) Merrifield, J. H.; Strouse, C. E.; Gladysz, J. A. Organometallics 1982, 1, 1204.
46. (b) Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865.
47. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
48. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176; Angew. Chem. 2002, 114, 4350.
49. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176; Angew. Chem. 2002, 114, 4350.
50. Perrin, D. D. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution, 2nd ed.; Pergamon: New York, 1982.
51. Jiao, H.; Le Stang, S.; Soós, T.; Meier, R.; Kowski, K.; Rademacher, P.; Jafarpour, L.; Hamard, J.-B.; Nolan, S. P.; Gladysz, J. A. J. Am. Chem. Soc. 2002, 124, 1516, and references therein.
52. 3 complex, see: Meyer, O.; Arif, A. M.; Gladysz, J. A. Organometallics 1995, 14, 1844.
53. Friedlein, F. K.; Hampel, F.; Gladysz, J. A. Manuscript in preparation.
54. (a) Cammidge, A. N.; Crépy, K. V. L. Chem. Commun. 2000, 1723.
55. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051.
56. (c) Castanet, A.-S.; Colobert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry 2002, 73, 659.
57. (d) Willis, M. C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem., Int. Ed. 2004, 43, 1249; Angew. Chem. 2004, 116, 1269.
58. (d) Willis, M. C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem., Int. Ed. 2004, 43, 1249; Angew. Chem. 2004, 116, 1269.
59. (e) Cammidge, A. N.; Crépy, K. V. L. Tetrahedron 2004, 60, 4377.
60. Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Organomet. Chem. 1997, 542, 281.
61. Jia, G.; Morris, R. H. J. Am. Chem. Soc. 1991, 113, 875.
62. Patton, A. T.; Strouse, C. E.; Knobler, C. B.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5804.
63. 7,18a
64. Zhou, Y.; Dewey, M. A.; Gladysz, J. A. Organometallics 1993, 12, 3918.
65. 3 and PPhPh' signals were not observed.
66. 2H is pyrophoric and was stored at -32°C in a glovebox. Preparation: (a) Parshall, G. W. Inorg. Synth. 1968, 11, 157. (b) King, R. B.; Cloyd, J. C., Jr. J. Am. Chem. Soc. 1975, 97, 46.
67. 2H is pyrophoric and was stored at -32°C in a glovebox. Preparation: (a) Parshall, G. W. Inorg. Synth. 1968, 11, 157. (b) King, R. B.; Cloyd, J. C., Jr. J. Am. Chem. Soc. 1975, 97, 46.
68. 18a
69. Tentative assignment
70. Zapf, A.; Beller, M. Chem. Eur. J. 2000, 6, 1830.
71. (a) "Collect" data collection software, Nonius B.V., 1998.
72. (b) "Scalepack" data processing software: Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276 (Macromolecular Crystallography, Part A), 307.
73. Sheldrick, G. M. SHELX-97, Program for refinement of crystal structures; University of Göttingen, 1997.
74. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography, Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974.