Palladium-catalyzed allylation of pronucleophiles with alkynes at 50°C - Remarkable effect of 2-(dicyclohexylphosphanyl)-2′-(dimethylamino) biphenyl as ligand

European Journal of Organic Chemistry

Volumn , Issue 18, 2006, Pages 4211-4213

  Patil, Nitin T ^a   Song, Dschun ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkynes; Allylation; Biphenyl ligands; Lower temperatures; Palladium; Pronucleophiles

Indexed keywords

EID: 33748762521     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600337     Document Type: Article

References (38)

1. a) J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, New York, 2000, Chapter 4;
2. b) M. Johannsen, K. A. Jorgensen, Chem. Rev. 1998, 98, 1689-1708;
3. c) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
4. d) A. Heumann, M. Reglier, Tetrahedron 1995, 51, 975-1015;
5. e) T. Hayashi, in: Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, 1993;
6. f) M. Sawamura, Y. Ito, Chem. Rev. 1992, 92, 857-871;
7. g) J. C. Fiaud, in: Metal-Promoted Selectivity in Organic Synthesis (Eds.: M. Graziani, A. J. Hubert, A. F. Noels), Kluwer Academic, Dordrecht, 1991;
8. h) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276;
9. i) B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837.
10. Y. Yamamoto, U. Radhakrishnan, Chem. Soc. Rev. 1999, 28, 199-207 and references cited therein.
11. a) B. M. Trost, Science 1991, 254, 1471-1477;
12. b) B. M. Trost, Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
13. a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263;
14. b) N. T. Patil, I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, Adv. Synth. Catal. 2004, 346, 800-804;
15. c) N. T. Patil, Y. Yamamoto, J. Org. Chem. 2004, 69, 6478-6481;
16. d) N. T. Patil, H. Wu, I. Kadota, Y. Yamamoto, J. Org. Chem. 2004, 69, 8745-8750.
17. a) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571;
18. b) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles 2002, 58, 347-357;
19. c) M. L. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 1622-1623;
20. [4d];
21. e) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210;
22. f) G. B. Bajracharya, Z. Huo, Y. Yamamoto, J. Org. Chem. 2005, 70, 4883-4886.
23. For a related reference, see; g) W. Zhang, A. R. Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578;
24. h) B. M. Trost, W. Brieden, K. H. Baringhaus, Angew. Chem. Int. Ed. Engl. 1992, 31, 1335-1336.
25. N. T. Patil, N. F. Khan, Y. Yamamoto, Tetrahedron Lett. 2004, 45, 8497-8499.
26. J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158-1174.
27. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696.
28. Palladium-catalyzed isomerization of alkynes to allenes, see: a) H. Sheng, S. Lin, Y. Huang, Tetrahedron Lett. 1986, 27, 4893-4894;
29. b) B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303;
30. c) X. Lu, J. Ji, D. Ma, W. Shen, J. Org. Chem. 1991, 56, 5774-5778.
31. For leading references, see: a) K. W. Anderson, M. Mendez-Perez, J. Priego, S. L. Buchwald, J. Org. Chem. 2003, 68, 9563-9573;
32. b) A. V. Vorogushin, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 8146-8149;
33. c) S.-i. Kuwabe, K. E. Torraca, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 12202-12206;
34. d) M. C. Harris, X. Huang, S. L. Buchwald, Org. Lett. 2002, 4, 2885-2888;
35. e) K. E. Torraca, X. Huang, C. A. Parrish, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 10770-10771;
36. f) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696.
37. a) P. Dotta, P. G. A. Kumar, P. S. Pregosin, Organometallics 2004, 23, 4247-4254;
38. b) P. Kocovsky, A. V. Malkov, S. Vyskocil, G. C. Lloyd-Jones, Pure Appl. Chem. 1999, 71, 1425-1433.