Synthesis, structural, and electron topographical analyses of a dialkylbiaryl phosphine/arene-ligated palladium(I) dimer: Enhanced reactivity in Suzuki-Miyaura coupling reactions

Journal of the American Chemical Society

Volumn 128, Issue 3, 2006, Pages 898-904

  Barder, Timothy E ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL BONDS; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ELECTRON TOPOGRAPHICAL ANALYSES; ENHANCED REACTIVITY; SUZUKI-MIYAURA COUPLING REACTIONS;

DIMERS;

BIS[2 (DICYCLOHEXYLPHOSPHINO) 2',6' DIMETHOXYBIPHENYL]PALLADIUM CHLORIDE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIMERIZATION; ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PRODUCT RECOVERY; REACTION TIME; SUZUKI REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIPHENYL COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES;

EID: 31444439688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0558995     Document Type: Article

References (37)

1. (a) Negishi, E. Acc. Chem. Res. 1982, 15, 340-348.
2. (b) Negishi, E.; de Meijere, A., Eds. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
3. st Century; John Wiley & Sons Ltd.: Chichester, West Sussex, U.K., 2004.
4. (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
5. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871-1876.
6. (c) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028-13032.
7. (d) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
8. Barder, T. E.; Buchwald, S. L. Unpublished results.
9. Kocovsky, P.; Vyskocil, S.; Cisarova, I.; Sejbal, J.; Tislerova, I.; Smrcina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714-7715.
10. (a) Murahashi, T.; Kurosawa, H. Coord. Chem. Rev. 2002, 231, 207-228.
11. (b) Kurosawa, H. J. Organomet. Chem. 2004, 689, 4511-4520.
12. 2 interaction between Pd and one of the olefins of dba where the Pd-C bond critical points have ellipticity values of 0.7829 and 0.3077.
13. (a) Allegra, G.; Immirzi, A.; Porri, L. J. Am. Chem. Soc. 1965, 87, 1394-1395.
14. (b) Allegra, G.; Cassagrande, G. T.; Immirzi, A.; Porri, L.; Vitulli, G. J. Am. Chem. Soc. 1970, 92, 289-293.
15. Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216.
16. Dupont, J.; Pfeffer, M.; Rotteveel, M. C.; De Cian, A.; Fischer, J. Organometallics 1989, 8, 1116-1118.
17. Budzelaar, P. H. M.; Van Leeuwen, P. W. N. M.; Roobeek, C. F.; Orpen, A. G. Organometallics 1992, 11, 23-25.
18. Christmann, U.; Vilar, R.; White, A. J. P.; Williams, D. J. Chem. Commun. 2004, 1294-1295.
19. Murahashi, T.; Otani, T.; Mochizuki, E.; Kai, Y.; Kurosawa, H. J. Am. Chem. Soc. 1998, 120, 4536-4537.
20. Olah, G. A. J. Am. Chem. Soc. 1971, 94, 808-820.
21. Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978-13980 and references therein.
22. (a) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861-2873.
23. (b) Jørgensen, M.; Lee, S.; Liu, X.-X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
24. (c) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746-4748.
25. Bader, R. F. W. Atoms in Molecules; Oxford University Press: New York, 2003.
26. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397-5403.
27. Silvi, B.; Savin, A. Nature 1994, 371, 683-686.
28. Frisch, M. J., et al. Gaussian 03, revision B.05: Gaussian, Inc.: Pittsburgh, PA, 2003.
29. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
30. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
31. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
32. Biegler-König, F.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545-559.
33. Kohout, M. DGRID, edition 3.0; Max Planck Institute of Chemical Physics of Solids: Dresden, 2005.
34. Humphrey, W.; Dalke, A.; Schulten, K. VMD - Visual Molecular Dynamics. J. Mol. Graphics 1996, 14, 33-38.
35. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. MOLEKEL 4.0; Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
36. 2+.
37. Koritsanszky, T.; Buschmann, J.; Luger, P. J. Phys. Chem. 1996, 100, 10547-10553.