Oxidative addition of phenyl bromide to Pd(BINAP) vs Pd(BINAP)(amine). Evidence for addition to Pd(BINAP)

Organic Letters

Volumn 8, Issue 5, 2006, Pages 851-854

  Shekhar, Shashank ^a   Ryberg, Per ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BINAP, 2 NAPHTHOL; BINAP, 2-NAPHTHOL; BROMIDE; NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS; THERMODYNAMICS;

BENZENE DERIVATIVES; BROMIDES; CATALYSIS; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; THERMODYNAMICS;

EID: 33644962633     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0528890     Document Type: Article

References (35)

1. (a) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
2. (b) Jutand, A. J. Organomet. Chem. 1999, 576, 254.
3. (a) Fauvarque, J.-F.; Pflüger, F. J. Organomet. Chem. 1981, 208, 419.
4. (b) Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276.
5. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
6. Barios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944.
7. (a) Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618.
8. (b) Alcazar-Roman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491.
9. (a) Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176.
10. (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
11. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
12. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
13. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
14. (e) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, p 1051.
15. (f) Hartwig, J. F. In Modern Arene Chemistry; Astruc, C., Ed.; Wiley-VCH: Weinheim, Germany, 2002, p 107.
16. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
17. (b) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
18. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
19. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
20. (e) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
21. (f) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 44, 1371.
22. Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104.
23. (a) Otsuka, S. J. Organomet. Chem. 1980, 200, 191.
24. (b) Obara, S.; Kitamura, K.; Morokuma, K. J. Am. Chem. Soc. 1984, 106, 7482.
25. (c) Yoshida, T.; Yamagata, T.; Tulip, T. H.; Ibers, J. A.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 2063.
26. (d) Low, J. J.; W. A. G., III. J. Am. Chem. Soc. 1984, 106, 6928.
27. (e) Low, J. J.; W. A. G., III. Organometallics 1986, 5, 609.
28. (f) Hofmann, P.; Heiss, H.; Muller, G. Z. Naturforsch. 1987, B42, 395.
29. (g) Hofmann, P.; Padmanabhan, M. Organometallics 1983, 2, 1273.
30. (a) Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276.
31. (b) Fauvarque, J.-F.; Pfluger, F. J. Organomet. Chem. 1981, 208, 419.
32. 3a this experiment might be considered to have insufficiently addressed this issue because the concentration of amine in this experiment was much less than the concentration of amine in the catalytic system.
33. obs vs [PhBr], and the absence of accumulation of intermediates demonstrate that path C cannot be the major pathway because path C would be first order in [ArBr] at all concentrations (see Supporting Information for data).
34. 13 Data with this bromoarene are provided as Supporting Information.
35. Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, in press.