Novel and convenient method for the stereo-and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes

Journal of the American Chemical Society

Volumn 107, Issue 4, 1985, Pages 972-980

  Miyaura, Norio ^a   Yamada, Kinji ^a   Suginome, Hiroshi ^a   Suzuki, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ORGANIC COMPOUNDS;

1-ALKENYLBORANES; CONJUGATED ALKADIENES; PALLADIUM-CATALYZED CROSS-COUPLING REACTION; REGIOSPECIFIC SYNTHESIS;

ORGANOMETALLICS;

EID: 0022012266     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00290a037     Document Type: Article

References (45)

1. (2) Dang, H. P.; Linstrumelle, G. Tetrahedron Lett. 1978, 191–194.
2. (7) Whitesides, G. M.; Casey, C. P.; Krieger, J. K. J. Am. Chem. Soc. 1971, 93, 1379–1389.
3. (9) Okukado, N.; Van Horn, D. E.; Klima, W. L.; Negishi, E. Tetrahedron Lett. 1978, 1027–1030.
4. (10) Brown, H. C. “Organic Synthesis via Boranes”; Wiley: New York, 1975.
5. (11) Cragg, G. M. L. “Organoboranes in Organic Synthesis”; Marcel Dekker: New York, 1973.
6. (12) Campbell, J. B., Jr.; Molander, G. A. J. Organomet. Chem. 1978, 156, 71–79.
7. (13) Larock, R. C.; Mitchell, M. A. J. Am. Chem. Soc. 1978, 100, 180-188.
8. (15) Miyaura, N.; Suzuki, A. J. Organomet. Chem. 1981, 213, C53-56.
9. (17) Zask, A.; Helquist, P.J. Org. Chem. 1978, 43, 1619–1620.
10. (18) Maitlis, P. T. “Organic Chemistry of Palladium”; Academic Press: New York, 1971; Vol. 2.
11. (19) Onoue, H.; Moritani, I.; Murahashi, S.-I. Tetrahedron Lett. 1973, 121–124.
12. (20) Robinson, S. D.; Shaw, B. L. J. Organomet. Chem. 1965, 3, 367–370.
13. (21) Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 993–999.
14. (22) Larock, R. C. “New Applications of Organometallic Reagents in Organic Synthesis”; Seyferth, D., Ed.; Elsevier: Amsterdam, 1976.
15. (24) Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434–442.
16. (25) Miyaura, N.; Suzuki, A. Chem. Lett. 1981, 879–881.
17. (26) Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866–867.
18. (27) Miyaura, N.; Yano, T.; Suzuki, A. Tetrahedron Lett. 1980, 21, 2865–2868.
19. (28) Miyaura, N.; Tanabe, Y.; Suginome, H.; Suzuki, A. J. Organomet. Chem. 1982, 233, C13-16.
20. (29) Miyaura, N.; Maeda, K.; Suginome, H.; Suzuki, A. J. Org. Chem. 1982, 47, 2117–2120. 1982
21. (30) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513–519.
22. (31) Rossi, R.; Carpita, A.; Quiricci, M. G. Tetrahedron 1981, 37, 2617–2623.
23. (32) Cassani, G.; Massardo, P.; Piccardi, P. Tetrahedron Lett. 1983, 24, 2513–2516.
24. (33) Miyaura, N.; Suginome, H.; Suzuki, A. Bull. Chem. Soc. Jpn. 1982, 55, 2221–2223.
25. (35) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1984, 25, 761–764.
26. (37) Brandsma, L. “Preparative Acetylenic Chemistry” Elsevier: Amsterdam, 1971.
27. (38) Lane, C. F. Tetrahedron 1976, 32, 981–990.
28. (39) Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1971, 93, 1816–1818.
29. (40) Brown, H. C.; Gupta, S. K. J. Am. Chem. 1972, 94, 4370–4373.
30. (41) Cristol, S. J.; Norris, W. P. J. Am. Chem. Soc. 1953, 75, 2645–2646.
31. (42) Miller, R. B.; Reichenbach, T. Tetrahedron Lett. 1974, 543–546.
32. (43) Brown, H. C.; Hamaoka, T.; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 6456–6457.
33. (44) Ashworth, F.; Burkhardt, G. N. J. Chem. Soc. 1928, 1791–1802.
34. (45) Farrell, J. K.; Bachman, G. B. J. Am. Chem. Soc. 1935, 57, 1281-1283.
35. (46) Schulte, K. E.; Goes, M. Arch. Pharm. (Weinheim, Ger.) 1957, 290, 118–130.
36. (47) Miller, S. I.; Ziegler, G. R.; Wieleseck, R. Org. Synth. 1963, 5, 921–923.
37. (48) Hurd, C. D.; Schmerling, L. J. Am. Chem. Soc. 1937, 59, 107–109.
38. (49) Kharasch, M. R.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882–884.
39. (50) Coulson, D. R. Inorg. Synth. 1972, 13, 121–123.
40. (51) Robinson, S. O.; Shaw, B. L. J. Organomet. Chem. 1965, 3, 367–370.
41. (52) Fitton, P.; Mekeon, J. E. J. Chem. Soc., Chem. Commun. 1968, 4–5.
42. (53) Zweifel, G.; Polston, NL. J. Am. Chem. Soc. 1970, 42, 4068–4071
43. (55) Miyaura, N.; Yano, T.; Suzuki, A. Bull. Chem. Soc. Jpn. 1980, 53, 1471–1472.
44. (56) Miyaura, N.; Itoh, M.; Suzuki, A. Tetrahedron Lett. 1976, 255–258.
45. (57) McDonald, R. N.; Campbell, T. W. Org. Synth. 1960, 40, 36–38.