Reductive elimination of aryl halides upon addition of hindered alkylphosphines to dimeric arylpalladium(II) halide complexes

Organometallics

Volumn 23, Issue 7, 2004, Pages 1533-1541

  Roy, Amy H ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPLEXATION; PHOSPHORUS COMPOUNDS; REACTION KINETICS; REDUCTION; SUBSTITUTION REACTIONS; THERMODYNAMIC PROPERTIES;

ALKYLPHOSPHINES; ARYL HALIDES; DIMERIC ARYLPALLADIUM HALIDE COMPLEXES; LIGANDS; REDUCTIVE ELIMINATION;

PALLADIUM COMPOUNDS;

EID: 1842640096     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034277u     Document Type: Article

References (35)

1. Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 573, 254.
2. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434.
3. Heck, R. F. Org. React. 1982, 27, 345.
4. Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
5. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
6. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
7. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
8. Stanforth, S. P. Tetrahedron 1998, 54, 263.
9. Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: New York, 2002; Vol. 1, p 229.
10. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
11. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
12. Hartwig, J. F. In Modern Animation Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000; p 195.
13. Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
14. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
15. Mann, G.; Incarvito, C.; Rheingold, A.L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
16. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
17. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
18. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360.
19. Ettorre, R. Inorg. Nucl. Chem. Lett. 1969, 5, 45.
20. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944.
21. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987.
22. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley & Sons: New York, 2001.
23. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
24. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
25. Tolman, C. A. Chem. Rev. 1977, 77, 313.
26. Stambuli, J. P.; Buhl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
27. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
28. Yoshida, T.; Otsuka, S. J. Am. Chem. Soc. 1977, 99, 2134.
29. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 1232.
30. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 7.
31. Widenhoefer, R.; Buchwald, S. L. Organometallics 1996, 15, 2755.
32. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem. Eur. J. 2001, 7, 1703.
33. Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89.
34. Connors, K. A. Chemical Kinetics. The Study of Reaction Rates in Solution; Wiley-VCH: New York, 1990.
35. Kuzmic, P. Anal. Biochem. 1996, 237, 260.