Rhodium-catalyzed conjugate addition of aryl- or 1-alkenylboronic acids to enones

Organometallics

Volumn 16, Issue 20, 1997, Pages 4229-4231

  Sakai, Masaaki ^a   Hayashi, Hiroyuki ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5244346814     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9705113     Document Type: Article

References (31)

1. (a) Posner, G. H. Org. React. 1972, 19, 1.
2. (b) Lipshutz, B. H. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; pp 283-382.
3. Greene, A. E.; Lansard, J.-P.; Luche, J.-L.; Petrier, C. J. Org. Chem. 1984, 49, 931. Pettier, C.; Barbosa, J. C. S.; Dupuy, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 5761. Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. Bolm, C. Tetrahedron: Asymmetry 1991, 2, 701.
4. Greene, A. E.; Lansard, J.-P.; Luche, J.-L.; Petrier, C. J. Org. Chem. 1984, 49, 931. Pettier, C.; Barbosa, J. C. S.; Dupuy, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 5761. Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. Bolm, C. Tetrahedron: Asymmetry 1991, 2, 701.
5. Greene, A. E.; Lansard, J.-P.; Luche, J.-L.; Petrier, C. J. Org. Chem. 1984, 49, 931. Pettier, C.; Barbosa, J. C. S.; Dupuy, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 5761. Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. Bolm, C. Tetrahedron: Asymmetry 1991, 2, 701.
6. Greene, A. E.; Lansard, J.-P.; Luche, J.-L.; Petrier, C. J. Org. Chem. 1984, 49, 931. Pettier, C.; Barbosa, J. C. S.; Dupuy, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 5761. Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. Bolm, C. Tetrahedron: Asymmetry 1991, 2, 701.
7. (a) Loots, M. J.; Schwartz, J. J. Am. Chem. Soc. 1977, 99, 8045.
8. (b) Dayrit, F. M.; Gladkowski, D. E.; Schwartz, J. Ibid. 1980, 102, 3976.
9. Ashby, E. C.; Heinsohn, G. J. Org. Chem. 1974, 39, 3297. Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244.
10. Ashby, E. C.; Heinsohn, G. J. Org. Chem. 1974, 39, 3297. Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244.
11. Cacchi, S.; Palmieri, G. J. Organomet. Chem. 1985, 282, C3.
12. (a) Nikishin, G. I.; Kovalev, I. P. Tetrahedron Lett. 1990, 31, 7063.
13. (b) Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Misawa, H.; Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565.
14. (c) Trost, B. M. Angew. Chem. 1995, 107, 285.
15. (a) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuno, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
16. (b) Sawamura, M.; Sudoh, M.; Ito, Y. Ibid. 1996, 118, 3309.
17. Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S. J. Org. Chem. 1995, 60, 883.
18. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19. The bond angle affects the rate of CO insertion into the C-Pd bond, see: Dekker, G. P. C.; Elsevier, C. J.; Vrieze, K. Organometallics 1992, 11, 1598.
20. 20O: 204.1507. Found: 204.1500.
21. House, H. O.; Huber, L. E.; Umen, M. J. J. Am. Chem. Soc. 1972, 94, 8471.
22. The addition to other α,β-unsaturated aldehydes, nitriles, or esters is in progress; however, these reactions are very slow under the above reaction conditions.
23. Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
24. 2 with PhLi gives the corresponding phenylrhodium(I) complexes, see: Keim, W. J. Organomet. Chem. 1968, 14, 179. Hegedus, L. D.; Lo, S. M.; Bloss, D. E. J. Am. Chem. Soc. 1973, 95, 3040. However, the isolation and characterization of arylrhodium species need to be investigated further.
25. 2 with PhLi gives the corresponding phenylrhodium(I) complexes, see: Keim, W. J. Organomet. Chem. 1968, 14, 179. Hegedus, L. D.; Lo, S. M.; Bloss, D. E. J. Am. Chem. Soc. 1973, 95, 3040. However, the isolation and characterization of arylrhodium species need to be investigated further.
26. The hydrolysis of the rhodium(I) enolate with water to give a hydroxorhodium species and its transmetalation with arylboronic acid is another probable process to give a phenylrhodium(I) intermediate, see: Grushin, V. V.; Kuznetsov, V. F.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3927.
27. Suzuki, A.; Arase, A.; Matsumoto, H.; Itoh, M.; Brown, H. C.; Rogic, M. M.; Rathke, M. W. J. Am. Chem. Soc. 1967, 89, 5708.
28. Fujishima, H.; Takada, E.; Hara, S.; Suzuki, A. Chem. Lett. 1992, 695. Ishimura, S.; Hara, S.; Suzuki, A. Synlett 1996, 993.
29. Fujishima, H.; Takada, E.; Hara, S.; Suzuki, A. Chem. Lett. 1992, 695. Ishimura, S.; Hara, S.; Suzuki, A. Synlett 1996, 993.
30. Molander, G. A.; Shingaram, B.; Brown, H. C. J. Org. Chem. 1984, 49, 5024. Molander, G. A.; Brown, H. C. Ibid. 1977, 42, 3106.
31. Molander, G. A.; Shingaram, B.; Brown, H. C. J. Org. Chem. 1984, 49, 5024. Molander, G. A.; Brown, H. C. Ibid. 1977, 42, 3106.