Pd-catalyzed allylic substitution using nucleophilic N-heterocyclic carbene as a ligand

Organic Letters

Volumn 5, Issue 1, 2003, Pages 31-33

  Sato, Yoshihiro ^a   Yoshino, Taro ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; LIGAND; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0037800674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026961v     Document Type: Article

References (33)

1. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
2. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Herrmann, W. A.; Weskamp, T.; B6hm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1. (c) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
3. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1. (c) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
4. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1. (c) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
5. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1. (c) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
6. For reviews, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290. (b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1. (c) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (e) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
7. (a) Herrmann, W. A.; Reisinger, C. P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93.
8. (b) Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186.
9. (c) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
10. (d) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
11. (e) Zhang, C.; Trudell, M. L. Tetrahedron Lett. 2000, 41, 595.
12. (F) Fürstner, A.; Leitner, A. Synlett, 2001, 290.
13. (a) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
14. For Ni-catalyzed Kumada-Tamao cross-coupling reactions using nucleophilic N-heterocyclic carbenes, see: (b) Böhm, V. P. W.; Weskamp, T. ; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602.
15. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371.
16. (b) Herrmann, W. A.; Fischer, J.; Elison, M.; Köcher, C.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 772.
17. (c) Enders, D.; Gielen, H.; Raabe, G.; Runsink, J.; Teles, H. Chem. Ber. 1996, 129, 1483.
18. (d) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165.
19. (e) McGuinness, D. S.; Cavell, K. J. Organometallics 1999, 18, 1596.
20. (f) Clyne, D. S.; Jin, J.; Genest, E.; Gallucci, J. C.; RajanBabu, T. V. Org. Lett. 2000, 2, 1125.
21. (g) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
22. (a) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
23. (b) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
24. (a) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 616, 617.
25. (b) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020.
26. (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387.
27. (b) Tsuji, J. Acc. Chem. Res. 1969, 2, 144.
28. (a) Hata, G.; Takahashi, K.; Miyake, A. Chem. Commun. 1970, 1392.
29. (b) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821.
30. For reviews, see: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (b) Harrington, P. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science, Ltd.: Oxford, UK, 1995; Vol. 12, p 797. (c) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons, Ltd.: Chichester, UK, 1995.
31. For reviews, see: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (b) Harrington, P. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science, Ltd.: Oxford, UK, 1995; Vol. 12, p 797. (c) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons, Ltd.: Chichester, UK, 1995.
32. For reviews, see: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 385. (b) Harrington, P. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science, Ltd.: Oxford, UK, 1995; Vol. 12, p 797. (c) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons, Ltd.: Chichester, UK, 1995.
33. 2 and imidazolium salts by treatment with BuLi; see: Sato, Y.; Sawaki, R.; Mori, M. Organometallics 2001, 20, 5510.