Palladium-catalyzed cross-coupling reaction of triorganoindium reagents with propargylic esters

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1403-1406

  Riveiros, Ricardo ^a   Rodríguez, David ^a   Sestelo, José Pérez ^a   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645897044     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060192o     Document Type: Article

References (50)

1. (a) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267-1269.
2. (b) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155-4160.
3. For contributions of this group, see: (a) Pena, M. A.; Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. Chem. Commun. 2002, 2246-2247.
4. (b) Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A. Synthesis 2003, 780-784.
5. (c) Pena, M. A.; Pérez Sestelo, J.; Sarandeses, L. A. Synthesis 2005, 485-492.
6. For references from other groups, see: (a) Legros, J. Y.; Primault, G.; Fiaud, J. C. Tetrahedron 2001, 57, 2507-2514.
7. (b) Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2003, 5, 2993-2995.
8. (c) Lehmann, U.; Awasthi, S.; Minehan, T. Org. Lett. 2003, 5, 2405-2408.
9. (d) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokuho, H.; Oshima, K. J. Org. Chem. 2003, 68, 6627-6631.
10. (e) Qian, M. X.; Huang, Z. H.; Negishi, E. Org. Lett. 2004, 6, 1531-1534.
11. (f) Gopalsamuthiram, V.; Wulff, W. D. J. Am. Chem. Soc. 2004, 126, 13936-13937.
12. (g) Qian, M. X.; Negishi, E. I. Tetrahedron Lett. 2005, 46, 2927-2930.
13. (h) Fausett, B. W.; Liebeskind, L. S. J. Org. Chem. 2005, 70, 4851-4853.
14. (a) Lee, K.; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265-8268.
15. (b) Lee, P. H.; Lee, S. W.; Seomoon, D. Org. Lett. 2003, 5, 4963-4966.
16. (a) Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2003, 68, 2518-2520.
17. (b) Baker, L.; Minehan, T. J. Org. Chem. 2004, 69, 3957-3960.
18. (c) Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2004, 69, 8136-8139.
19. (a) Krause, N.; Hoffmann-Röder, A. In Modern Allene Chemistry: Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim. 2004; pp 997-1039.
20. (b) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196-1216.
21. (c) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470-10471.
22. Ma, S. In Modern Allene Chemistry: Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; pp 595-699.
23. Murakami, M.; Matsuda, T. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; pp 727-815.
24. (a) Brummond, K. M.; Chen, H. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; pp 1041-1090.
25. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31-48.
26. (c) Marshall, J. A. Chem. Rev. 2000, 100, 3163-3186.
27. Keinan, E.; Bosch, E. J. Org. Chem. 1986, 51, 4006-4016.
28. For general references, see: (a) Tsuji, J.; Mandai, T. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 585-618.
29. (b) Alexakis, A. Pure Appl. Chem. 1992, 64, 387-392.
30. (c) Hoffmann-Röder, A.; Krause, N. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim. 2004; pp 51-92.
31. (a) Pasto, D. J.; Hennion, G. F.; Shults, R. H.; Waterhouse, A.; Chou, S.-K. J. Org. Chem. 1976, 4l, 3496-3496.
32. (b) Jeffery-Luong, T.; Linstrumelle, G. Tetrahedron Lett. 1980, 21, 5019-5020.
33. (a) Negishi, E.; Liu, F. In Handbook of Organopalladium Chemistry for Organic Synthesis: Negishi, E., Ed.; Wiley: New York. 2002; pp 551-589.
34. (b) Kleijn, H.; Meijer, J.; Overbeek, G. C.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1982, 101, 97-101.
35. (c) Darcel, C.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 1845-1846.
36. (d) Dixneuf, P. H.; Guyot, T.; Ness, M. D.; Roberts, S. M. Chem. Commun. 1997, 2083-2084.
37. Other organometals have found isolated applications: Boron: (a) Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 149-151.
38. (b) Ishikura, M.; Matsuzaki, Y.; Agata, I.; Katagiri, N. Tetrahedron 1998, 54, 13929-13942.
39. Aluminum: (c) Keinan, E.; Bosh, E. J. Org. Chem. 1986, 51, 4006.
40. Tin: (d) Tsutsumi, K.; Ogoshi, S.; Kakiuchi, K.; Nishiguchi, S.; Kurosawa, H. Inorg. Chim. Acta 1998, 296, 37-44.
41. DPEphos = bis(o-(diphenylphosphino)phenyl) ether, (a) 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.
42. (b) Huang, Z.; Qian, M.; Babinski, D. J.; Negishi, E. Organometallics 2005, 24, 475-478.
43. N2′ propargylic reaction, see Supporting Information.
44. In the reaction, compound 8 (Table 2. entry 6) was also obtained as a major byproduct.
45. (a) Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103-1105.
46. (b) Konno, T.; Tanikawa, M.; Ishihara, T.; Yamanaka, H. Chem. Lett. 2000, 1360-1361.
47. (c) Yoshida, M.; Gotou, T.; Ihara, M. Tetrahedron Lett. 2004, 45, 5573-5575.
48. (d) Yoshida, M.; Ueda, H.; Ihara, M. Tetrahedron Lett. 2005, 46, 6705-6708.
49. Prepared from the corresponding commercially available alcohol. For further experimental details, see Supporting Information.
50. Mannschreck, A.; Munninger, W.; Burgermeister, T.; Gore, J.; Cazes, B. Tetrahedron 1986, 42, 399-408.