Palladium catalysed alkylative dimerization between pronucleophiles and vinyltins

Chemical Communications

Volumn , Issue 16, 1997, Pages 1583-1584

  Nakamura, Itaru ^a   Tsukada, Naofumi ^a   Al Masum, Mohammad ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008130183     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703463f     Document Type: Article

References (22)

1. For a review, see B. M. Trost, Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
2. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
3. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
4. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
5. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
6. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
7. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
8. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
9. For allenes: Y. Yamamoto, M. Al-Masum and N. Asao, J. Am. Chem. Soc., 1994, 116, 6019; Y. Yamamoto, M. Al-Masum, N. Fujiwara and N. Asao, Tetrahedron Lett., 1995, 36, 2833; Y. Yamamoto and M. Al-Masum, Synlett, 1995, 969; Y. Yamamoto, M. Al-Masum and N. Fujiwara, Chem. Commun., 1996, 381; Y. Yamamoto, M. Al-Masum and A. Takeda, Chem. Commun., 1996, 831; M. Meguro, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1996, 37, 7453. For other types of allene addition: B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc., 1995, 117, 5156; L. Besson, J. Goré and B. Cazes, Tetrahedron Lett., 1995, 36, 3853.
10. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
11. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
12. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
13. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
14. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
15. For 1,3-dienes: K. Takahashi, A. Miyake and G. Hata, Chem. Ind. (London), 1971, 488; K. Takahashi, A. Miyake and G. Hata, Bull. Chem. Soc. Jpn., 1972, 45, 1183; O. S. Andell, J. E. Bäckvall and C. Moberg, Acta Chem. Scand., Ser. B, 1986, 40, 184; P. W. Jolly and N. Kokel, Synthesis, 1990, 771; C. Mercier, G. Mignani, M. Aufrand and G. Allmang, Tetrahedron Lett., 1991, 32, 1433; B. M. Trost and L. Zhi, Tetrahedron Lett., 1992, 33, 1831.
16. For enynes: M. M. Salter, V. Gevorgyan, S. Saito and Y. Yamamoto, Chem. Commun., 1996, 17.
17. The Mitsunobu type reaction between trans-but-2-en-1,4-diol and pronucleophiles produced the corresponding 1,4-disubstituted butenes. Those authentic samples were compared with the alkylative dimerization products 3; O. Mitsunobu, Synthesis, 1981, 1.
18. Y. Yamamoto and N. Fujiwara, J. Chem. Soc., Chem. Commun., 1995, 2013.
19. N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 4568.
20. For palladium catalysed dimerization of alkenyistannanes, see S. Kanemoto, S. Matsubara, K. Oshima, K. Utimoto and H. Nozaki, Chem. Lett., 1987, 5; G. A. Tolstikov, M. S. Miftakhov, N. A. Danilova, Ya. L. Vel'der and L. V. Spirikhin, Synthesis, 1989, 633.
21. For palladium catalysed dimerization of alkenyistannanes, see S. Kanemoto, S. Matsubara, K. Oshima, K. Utimoto and H. Nozaki, Chem. Lett., 1987, 5; G. A. Tolstikov, M. S. Miftakhov, N. A. Danilova, Ya. L. Vel'der and L. V. Spirikhin, Synthesis, 1989, 633.
22. Y. Yamamoto and N. Tsukada, unpublished work, see also ref. 3.