Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12104-12105

  Kuwano, Ryoichi ^a   Kondo, Yutaka ^a   Matsuyama, Yosuke ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; ESTER; METAL COMPLEX; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; COUPLING FACTOR; ELECTRON TRANSPORT; LIGAND BINDING; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0141958026     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037735z     Document Type: Article

References (23)

1. (a) Hata, G.; Takahashi, K.; Miyake, A. J. Chem. Soc., Chem. Commun. 1970, 1392-1393.
2. (b) Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 230-236.
3. (c) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 11, 3821-3824.
4. (a) Roberts, J. S.; Klabunde, K. J. J. Am. Chem. Soc. 1977, 99, 2509-2515.
5. (b) Gatti, G.; López, J. A.; Mealli, C.; Musco, A. J. Organomet. Chem. 1994, 483, 77-89.
6. (a) Hayashi, T.; Matsumoto, Y.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 601-612.
7. (b) Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 2436-2448.
8. (c) LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906-907.
9. (d) Nozaki, K.; Komaki, H.; Kawashima, Y.; Hiyama, T.; Matsubora, T. J. Am. Chem. Soc. 2001, 123, 534-544.
10. (e) Nettekoven, U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166-1167.
11. (a) Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett. 1992, 33, 2509-2510.
12. (b) Legros, J.-Y.; Toffano, M.; Fiaud, J.-C. Tetrahedron 1995, 51, 3235-3246.
13. (c) Legros, J.-Y.; Toffano, M.; Fiaud, J.-C. Tetrahedron: Asymmetry 1995, 6, 1899-1902.
14. (d) Toffano, M.; Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett. 1997, 38, 77-80.
15. (e) Legros, J.-Y.; Primault, G. I.; Toffano, M.; Rivière, M.-A.; Fiaud, J.-C. Org. Lett. 2000, 2, 433-436.
16. 4-DPPF catalyst yielded neither 4a nor 5a in the absence of base.
17. Bite angles of DPPE, DPPP, DPPB, and DPPF in the palladium dichloride complexes are 86°, 91°, 95°, and 99°, respectively: (a) Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432-2439.
18. (b) Makhaev, V. D.; Dzhabieva, Z. M.; Konovalikhin, S. V.; D'yachenko, O. A.; Belov, G. P. Russ. J. Coord. Chem. 1996, 22, 563-567.
19. (c) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
20. Calculated values for the natural bite angles of DPEphos and Xantphos are 102° and 112° respectively: Kranenburg, M.; van der Burgt, Y. E. M. ; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081-3089.
21. Snyder, H. R.; Shekleton, J. F.; Lewis, C. D. J. Am. Chem. Soc. 1945, 67, 310-312.
22. We evaluated DPPF, DPEphos, and Xantphos for the reaction of 3a and 8a with 5 mol % of catalyst. GC yields (3 h) were 7%, 23%, and 8%, respectively.
23. No benzylic amine 9f was detected by GC analysis in the reaction of 3b and 8a at 80°C in DME without the palladium catalyst.