Palladium catalyzed hydrocarbonation of olefins

Pure and Applied Chemistry

Volumn 68, Issue 1, 1996, Pages 9-14

  Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002026470     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668010009     Document Type: Article

References (25)

1. a) L.S Hegedus, in Comprehensive Organic Synthesis; B.M. Trost and I. Fleming, Eds. Pergamon Press, vol.4, p571, Oxford, U.K. (1990).
2. b) For carbometallation, P. Knochel, in Comprehensive Organic Synthesis; B.M. Trost and I. Fleming, Eds. Pergamon Press, vol.4, p.865, Oxford, U.K. (1990).
3. Michael and aldol reactions, a) T. Naota, H. Taki, M. Mizuno, and S.-I. Murahashi, J. Am. Chem. Soc. 111, 5954 (1989). Michael reactions, b) S. Paganelli, A. Schionata, and C. Batteghi, Tetrahedron Lett. 32, 2807 (1991). c) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). Imine addition, d) Y. Yamamoto, N. Kubota, Y. Honda, H. Fukui, N. Asao, and H. Nemoto, J. Am. Chem. Soc. 116, 3161 (1994).
4. Michael and aldol reactions, a) T. Naota, H. Taki, M. Mizuno, and S.-I. Murahashi, J. Am. Chem. Soc. 111, 5954 (1989). Michael reactions, b) S. Paganelli, A. Schionata, and C. Batteghi, Tetrahedron Lett. 32, 2807 (1991). c) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). Imine addition, d) Y. Yamamoto, N. Kubota, Y. Honda, H. Fukui, N. Asao, and H. Nemoto, J. Am. Chem. Soc. 116, 3161 (1994).
5. Michael and aldol reactions, a) T. Naota, H. Taki, M. Mizuno, and S.-I. Murahashi, J. Am. Chem. Soc. 111, 5954 (1989). Michael reactions, b) S. Paganelli, A. Schionata, and C. Batteghi, Tetrahedron Lett. 32, 2807 (1991). c) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). Imine addition, d) Y. Yamamoto, N. Kubota, Y. Honda, H. Fukui, N. Asao, and H. Nemoto, J. Am. Chem. Soc. 116, 3161 (1994).
6. Michael and aldol reactions, a) T. Naota, H. Taki, M. Mizuno, and S.-I. Murahashi, J. Am. Chem. Soc. 111, 5954 (1989). Michael reactions, b) S. Paganelli, A. Schionata, and C. Batteghi, Tetrahedron Lett. 32, 2807 (1991). c) M. Sawamura, H. Hamashima, and Y. Ito, J. Am. Chem. Soc. 114, 8295 (1992). Imine addition, d) Y. Yamamoto, N. Kubota, Y. Honda, H. Fukui, N. Asao, and H. Nemoto, J. Am. Chem. Soc. 116, 3161 (1994).
7. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
8. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
9. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
10. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
11. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
12. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
13. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
14. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
15. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
16. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
17. Transition metal catalyzed reactions of allenes, see (a) B. Cazes, Pure & Appl. Chem. 62, 1867 (1990). (b) V. Gauthier, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 915 (1991). (c) N. Chaptal, V.C. Gotleland, C. Grandjean, B. Cazes, and J. Gore, Tetrahedron Lett. 32, 1795 (1991). (d) L. Besson, J. Bazin, J. Gore, and B. Cazes, Tetrahedron Lett. 35, 2881 (1994). (e) I. Shimizu and J. Tsuji, Chem. Lett. 233 (1984). (f) I. Shimizu, T. Sugiura, and J. Tsuji, J. Org. Chem. 50, 537 (1985). (g) R.C. Larock, S.Varaprath, H.H. Lau, and C.A. Fellows, J. Am. Chem. Soc. 106, 5274 (1984). (h) R.C. Larock, N.G. Berrios-Pena, and C.A. Fried, J. Org. Chem. 56, 2615 (1991). (i) S. Ma and E. Negishi, J. Org. Chem. 59, 4730 (1994). (j) B.M. Trost and G. Kottirsh, J. Am. Chem. Soc. 112, 2816 (1990). (k) M. Yamaguchi, K. Omata, and M. Hirama, Tetrahedron Lett. 35, 5689 (1994).
18. Y. Yamamoto, M. Al-Masum, and N. Asao, J. Am. Chem. Soc. 116, 6019 (1994).
19. 2.
20. Y. Yamamoto, M. Al-Masum, N. Fujiwara, and N. Asao, Tetrahedron Lett., 36, 2811 (1995).
21. More recently , hydropalladation mechanisum has been proposed in the related reactions. B. M. Trost and V. J. Gerusz, J. Am. Chem. Soc. 117, 5156 (1995).
22. Y. Yamamoto and M. Al-Masum, Synlett. in print (1995).
23. N. Vicart, B. Cazes, and J. Gore, Tetrahedron Lett., 36. 535 (1995). N. Chaptal, V. C.-Gotteland, C. Granjean, B. Cazes, and J. Gore, ibid., 32, 1795 (1991).
24. N. Vicart, B. Cazes, and J. Gore, Tetrahedron Lett., 36. 535 (1995). N. Chaptal, V. C.-Gotteland, C. Granjean, B. Cazes, and J. Gore, ibid., 32, 1795 (1991).
25. Y. Yamamoto and N. Fujiwara, unpublished results.