A synthesis of (E)-(1-organo-1-alkenyl)boronates by the palladium-catalyzed cross-coupling reaction of (E)-1,2-bis(boryl)-1-alkenes with organic halides: A formal carboboration of alkynes via the diboration-coupling sequence

Chemistry Letters

Volumn , Issue 12, 1996, Pages 1117-1118

  Ishiyama, Tatsuo ^a   Yamamoto, Masafumi ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002888768     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.1117     Document Type: Article

References (14)

1. D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, New York (1995).
2. H. C. Brown, Organic Syntheses via Boranes, John Wiley & Sons, New York (1975).
3. A. Suzuki, Pure & Appl. Chem., 58, 629 (1986).
4. T. Ishiyama, K.-i. Nishijima, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 7219 (1993).
5. B. M. Mikhailov, Pure & Appl. Chem., 39, 505 (1974).
6. T. Ishiyama, N. Matsuda, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993). T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, and N. Miyaura, Organometallics, 15, 713 (1996).
7. T. Ishiyama, N. Matsuda, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993). T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, and N. Miyaura, Organometallics, 15, 713 (1996).
8. Part of this study was presented at Symposium: Transition Metal-Catalyzed Cross Coupling Reactions. Mechanism, Structure, and Synthesis on the 209th ACS meeting in Anaheim, April, 1995.
9. S. D. Brown and R. W. Armstrong, J. Am. Chem. Soc., 118, 6331 (1996).
10. 1H NMR (400 MHz, CDCl3): δ 0.91 (t, 3H, J = 7.3 Hz), 1.26 (s, 12H), 1.3-1.4 (m, 2H), 1.4-1.5 (m, 2H), 2.28 (t, 2H, J = 7.6 Hz), 2.31 (s, 3H), 6.83 (s, 1H), 7.05 (d, 2H, J = 7.8 Hz), 7.23 (d, 2H, J = 7.8 Hz).
11. Similar regioselective cross-coupling at the terminal C-B bond was recently reported; G. Desurmont, R. Klein, S. Uhlenbrock, E. Laloë , L. Deloux, D. M. Giolando, Y. W. Kim, S. Pereira, and M. Srebnik, Organometallics, 15, 3323 (1996).
12. R. W. Hoffmann, K. Ditrich, and S. Fröch, Liebigs Ann. Chem., 1987, 977.
13. B. E. Segelstein, T. W. Butler, and B. L. Chenard, J. Org. Chem., 60, 12 (1995).
14. N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).