Palladium-Catalyzed Inter- and Intramolecular Cross-Coupling Reactions of B-Alkyl-9-Borabicyclo[3.3.1]nonane Derivatives with 1-Halo-1-alkenes or Haloarenes. Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration-Coupling Sequence

Journal of the American Chemical Society

Volumn 111, Issue 1, 1989, Pages 314-321

  Miyaura, Norio ^a   Ishiyama, Tatsuo ^a   Sasaki, Hirotomo ^a   Ishikawa, Masako ^a   Satoh, Makoto ^a   Suzuki, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750283011     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00183a048     Document Type: Article

References (44)

1. Preliminary communication of this work has appeared: Miyaura, N.; Ishiyama, T.; Ishikawa, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 6369.
2. For general reviews, see: Collman, J. P.; Hegedus, L. S. Principles, and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980. Kochi, J. K. Organometallic Mechanisms, and Catalysts; Academic: New York, 1978. Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: New York, 1985. Hartley, F. R. The Chemistry of the Metal-Carbon Bond; Patai, S., Ed.; Wiley: New York, 1985.
3. Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487. Tamura, M.; Kochi, J. K. Synthesis 1971, 303. Kochi, J. K. Acc. Chem. Res. 1974, 7, 351. Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599. Kwan, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 4903.
4. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374. Tamao, K.; Zembayashi, M.; Kiso, Y.; Kumada, M. J. Organomet. Chem. 1973, 55, C91. Tamao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Komada, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958. Kumada, M. Pure Appl. Chem. 1980, 52, 669. Hayashi, T.; Konishi, M.; Fukushima, M., Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
5. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
6. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298. Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
7. Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408. Kondo, K.; Murahashi, S. Tetrahedron Lett. 1979, 1237.
8. Kosugi, M.; Simizu, Y.; Migita, T. Chem. Lett. 1977, 1423. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109. 5478.
9. Giacomelli, G.; Lardicci, L. Tetrahedron Lett. 1978, 19, 2831. Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1980, 21, 2531.
10. Castle, P. L.; Widdowson, D. A. Tetrahedron Lett. 1986, 27, 6013.
11. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972. Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron 1983, 39, 3271. Miyaura, N.; Satoh, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745. Satoh, M.; Miyaura, N.; Suzuki, A. Chem. Lett. 1986, 1329. Ishiyama, T.; Miyaura, N.; Suzuki, A. Chem. Lett. 1987, 25. Suzuki, A. Acc. Chem. Res. 1982, 15, 178. Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
12. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513. See also: Gronowitz, S.; Lawitz, K. Chem. Scr. 1983, 22, 265. Thompson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49, 5237. Ishikura, M.; Kamada, M.; Terashima, M. Synthesis 1984, 936. Miller, R. B.; Dugar, S. Organornetallics 1984, 3, 1261. Sharp, M. J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997.
13. For reviews concerning the selective hydroboration, see: Brown, H. C. Organic Synthesis via Boranes; Wiley: New York, 1975. Cragg, G. M. L. Organoboranes in Organic Synthesis; Marcel Dekker: New York, 1973. Lane, C. F. Synthetic Reagents; Pizey, J. S., Ed.; Ellis Harwood: New York, 1977; Vol. 3. Mikhailov, Yu. N. Organoboron Compounds in Organic Synthesis; OPA: Amsterdam, 1984, Suzuki, A.; Dhillon, R. S. Topics in Current Chemistry; Springer-Verlag: Berlin, 1986; Vol. 130, p 23.
14. Uenishi, J.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756.
15. Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
16. Honeycutt, J. B.; Riddle, J. M. J. Am. Chem. Soc. 1959, 81, 2593. Honeycutt, J. B.; Riddle, J. M. J. Am. Chem. Soc. 1960, 82, 3051. Larock, R. C.; Brown, H. C. J. Am. Chem. Soc. 1970, 92, 2467. Larock, R. C. J. Organomet. Chem. 1974, 67, 353. Larock, R. C. J. Am. Chem. Soc. 1974, 72, 35.
17. Snyder, H. R.; Kuck, J. A.; Johnson, J. R. J. Am. Chem. Soc. 1938, 60, 105. Brown, H. C.; Hebert, N. C.; Snyder, C. H. J. Am. Chem. Soc. 1961, 83. 1001. Brown. H. C.; Snyder, H. C. J. Am. Chem. Soc. 1961, 83, 1002.
18. Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993. Anderson, C. B.; Burreson, B. J.; Michalowski, T. J. J. Org. Chem. 1976, 41, 1990. Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157. Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
19. Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2595. Godschalx, J.; Stille, J. K. Tetrahedron Lett. 1980, 21, 2599. Goliaszewski, A.; Schwartz, J. Tetrahedron 1984, 40, 5779 and references therein.
20. For a review on the synthesis of juvenile hormones, see: Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley-Interscience: New York, 1980; p 58.
21. Bottin, J.; Fetizon, M. J. Chem. Soc., Chem. Commun. 1971, 1087. Midland, M. M.; Kwon, Y. C. J. Org. Chem. 1981, 46, 229.
22. Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
23. Boardman, L. D.; Bagheri, V.; Sawada, H.; Negishi, E. J. Am. Chem. Soc. 1984, 106, 6015. Negishi, E. Acc. Chem. Res. 1987, 20, 65.
24. Bestmann, H. J. Justus Liebigs Ann. Chem. 1968, 718, 24.
25. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245.
26. Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731. Satoh, Y.; Serizawa, H.; Hara, S.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 5225. Suzuki, A. Pure Appl. Chem. 1986, 58, 629.
27. Cousseau, J. Synthesis 1980, 805.
28. Stork, G.; Baine, N. H. J. Am. Chem. Soc. 1982, 104, 2321. Stork, G. Selectivity—A Goal for Synthetic Efficiency; Bartmann, W., Trost, B. M. Eds.; Verlag Chem.: Weinheim, 1984. Beckwith, A. L. J.; Gara, W. B. J. Am. Chem. Soc. 1979, 91, 5691.
29. Piers, E.; Gavai, A. V. Tetrahedron Lett. 1986, 27, 313. Shibasaki, M.; Sodeoka, M.; Ogawa, Y. J. Org. Chem. 1984, 49, 4096. Negishi, E.; Zhang, Y.; Cederbaum, F. E.; Webb, M. B. J. Org. Chem. 1986, 51, 4080. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1987, 109, 4755.
30. Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1974, 73, 1.
31. Brown, H. C.; Imai, T. J. Am. Chem. Soc. 1983, 105, 6285.
32. Murahashi, S.; Naota, T.; Tanigawa, Y. Org. Synth. 1984, 62, 39.
33. Farrell, J. K.; Bachman, G. B. J. Am. Chem. Soc. 1935, 57, 1281.
34. Bordwell, F. C.; Landis, P. S. J. Am. Chem. Soc. 1957, 79, 1593.
35. Canbere, P. Bull. Soc. Chim. Fr. 1964, 144.
36. Clark, R. D.; Ellis, J. E.; Heathcock, C. H. Synth. Commun. 1975, 5, 193.
37. Janssen, D. E.; Wilson, C. V. Org. Synth. 1963, 4, 547.
38. Vessiere, R.; Theron, F. Compt. Rend. 1965, 260, 597.
39. Leopold, E. J. Org. Synth. 1985, 64, 164.
40. Kent, R. E.; McElvain, S. M. Org. Synth. 1955, 3, 493.
41. Gassman, P. G.; Armour, E. A. Tetrahedron Lett. 1971, 1431.
42. Sondheimer, F.; Mechoulam, R. J. Am. Chem. Soc. 1958, 80, 3087.
43. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
44. Chatt, J.; Mann, F. G. J. Chem. Soc. 1939, 16.