Syntheses and thermolysis of arylpalladium hydroxide complexes: Implications for C(sp 2)-OH bond-forming reductive elimination to generate phenol derivatives

Organometallics

Volumn 31, Issue 3, 2012, Pages 1073-1081

  Hayashi, Yumi ^a   Wada, Shinji ^a   Yamashita, Makoto ^a,b   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOND FORMING; CESIUM HYDROXIDES; DFT CALCULATION; DINUCLEAR; HALIDE COMPLEXES; HYDROXO LIGANDS; IODIDE COMPLEX; KINETIC EQUATIONS; NEGATIVE ENTROPIES; P-NITROPHENOL; PHENOL DERIVATIVES; POLAR SOLVENTS; RATE CONSTANT K; REDUCTIVE ELIMINATION; SOLVENT MOLECULES; TRANSITION STATE;

CESIUM; CESIUM IODIDE; DENSITY FUNCTIONAL THEORY; HYDROGEN BONDS; INTEGRAL EQUATIONS; LIGANDS; PHENOLS; RATE CONSTANTS; THERMOLYSIS;

PALLADIUM COMPOUNDS;

EID: 84856897833     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om201142s     Document Type: Article

References (46)

1. Hartwig, J. F. Reductive Elimination. In Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010; Chapter 8.
2. Hartwig, J. F. Inorg. Chem. 2007, 46, 1936-1947
3. Haggin, J. Chem. Eng. News 1993, 71, 23-27
4. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398
5. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514
6. Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109-13110
7. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787-6795
8. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504-6511
9. Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225
10. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718-10719
11. Mann, G.; Shelby, Q.; Roy, A. H.; Hartwig, J. F. Organometallics 2003, 22, 2775-2789
12. Stambuli, J. P.; Weng, Z.; Incarvito, C. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2007, 46, 7674-7677
13. Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075-2077
14. Matsunaga, P. T.; Mavropoulos, J. C.; Hillhouse, G. L. Polyhedron 1995, 14 (1) 175-189
15. Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135-8136
16. Koo, K.; Hillhouse, G. L. Organometallics 1998, 17, 2924-2925
17. Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790-12791
18. Desai, L. V.; Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737-5740
19. Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 10974-10983
20. Oloo, W.; Zavalij, P. Y.; Zhang, J.; Khaskin, E.; Vedernikov, A. N. J. Am. Chem. Soc. 2010, 132, 14400-14402
21. Williams, B. S.; Holland, A. W.; Goldberg, K. I. J. Am. Chem. Soc. 1999, 121, 252-253
22. Williams, B. S.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 2576-2587
23. Smythe, N. A.; Grice, K. A.; Williams, B. S.; Goldberg, K. I. Organometallics 2009, 28, 277-288
24. Vedernikov, A. N.; Binfield, S. A.; Zavalij, P. Y.; Khusnutdinova, J. R. J. Am. Chem. Soc. 2006, 128, 82-83
25. Khusnutdinova, J. R.; Zavalij, P. Y.; Vedernikov, A. N. Organometallics 2007, 26, 3466-3483
26. Khusnutdinova, J. R.; Zavalij, P. Y.; Vedernikov, A. N. Organometallics 2007, 26, 2402-2413
27. Khusnutdinova, J. R.; Newman, L. L.; Zavalij, P. Y.; Lam, Y.-F.; Vedernikov, A. N. J. Am. Chem. Soc. 2008, 130, 2174-2175
28. Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694-10695
29. Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918-921
30. Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595-7599
31. Dumrath, A.; Wu, X.-F.; Neumann, H.; Spannenberg, A.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 8988-8992
32. Chen, G.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473-476
33. 3 by reductive elimination. See: Norton, D. M.; Mitchell, E. A.; Botros, N. R.; Jessop, P. G.; Baird, M. C. J. Org. Chem. 2009, 74, 6674-6680
34. Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; Garcia-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661-1664
35. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552-13554
36. Kashiwabara, T.; Tanaka, M. Tetrahedron Lett. 2005, 46, 7125-7128
37. Yagyu, T.; Hamada, M.; Osakada, K.; Yamamoto, T. Organometallics 2001, 20, 1087-1101
38. (Pan, Y.; Young, G. B. J. Organomet. Chem. 1999, 577, 257-264)
39. Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; Garcia-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661-1664
40. Furuya, T.; Benitez, D.; Tkatchouk, E.; Strom, A. E.; Tang, P.; Goddard, W. A.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 3793-3807
41. Goldberg, K. I.; Yan, J.; Breitung, E. M. J. Am. Chem. Soc. 1995, 117, 6889-6896
42. 2] was calculated. See: Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715-723
43. + was calculated. See: Zhang, X.; Schwarz, H. Theor. Chem. Acc. 2011, 129, 389-399
44. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250
45. Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Organometallics 1988, 7, 1363-1367
46. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961-5976