Cationic palladium complex-catalyzed cyclization-hydrosilylation of 1-alkene-6,11-diyne derivatives: Facile cyclization at the enyne part than at the diyne counterpart

Chemistry Letters

Volumn 35, Issue 8, 2006, Pages 846-847

  Shimamoto, Takamitsu ^a   Hirano, Tomohiro ^a   Nishimoto, Hiroyuki ^a   Yamamoto, Keiji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

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EID: 33750707261     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.846     Document Type: Article

References (21)

1. T. Uno, S. Wakayanagi, Y. Sonoda, K. Yamamoto, Synlett 2003, 1997.
2. 3 catalyzed by a cationic Pt complex, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, R. A. Widenhoefer, J. Org. Chem. 2002, 67, 2778, and references therein;
3. 3. see: K. Tamao, K. Kobayashi, Y. Ito, J. Am. Chem. Soc. 1989, 111, 6478;
4. K. Tamao, K. Kobayashi, Y. Ito, Synlett 1992, 539;
5. 3, see: T. Muraoka, I. Matsuda, K. Itoh, Organometallics 2002, 21, 3650;
6. T. Muraoka, I. Matsuda, K. Itoh, Tetrahedron Lett. 1998, 39, 7325;
7. I. Ojima, A. T. Vu, J. V. McCullagh, A. Kinoshita, J. Am. Chem. Soc. 1999, 121, 3230;
8. I. Ojima, S.-Y. Lee, J. Am. Chem. Soc. 2000, 122, 2385;
9. For a related work, see: C. Liu, R. A. Widenhoefer, Organometallics 2002, 21, 5666.
10. S. Wakayanagi, T. Shimamoto, M. Chimori, K. Yamamoto, Chem. Lett. 2005, 34, 160.
11. T. Shimamoto, M. Chimori, H. Sogawa, K. Yamamoto, J. Am. Chem. Soc. 2005, 127, 16410.
12. 3): δ 15.0, 18.2, 18.3 (x3), 23.9, 28.3, 28.5, 28.6, 35.3, 39.2, 58.3 (x3), 68.1, 84.8, 114.2, 149.6.
13. 13CNMR: δ 3.5, 15.0, 18.28 (x3), 18.29, 23.9, 28.5, 28.6, 29.1, 35.3, 39.2, 58.3 (x3), 75.4, 79.4, 118.3, 149.3.
14. 3Si: C, 67.40; H, 10.12%. Found: C, 67.15; H, 9.93%.
15. 5, 29.1, 35.3, 39.3, 58.0 (x2), 75.4, 79.4, 118.3, 149.3.
16. NMR spectral data of 10A and 10B have been given in Ref. 3 (Also, see Supporting Information).
17. Y. Kawanami K. Yamamoto, Synlett 1995, 1232;
18. Also, see: T. Sonoda, M. S. Thesis, Tokyo University of Science, Yamaguchi, 2003.
19. 13C NMR: δ 3.6, 14.7, 18.4 (x3), 23.9, 28.7, 34.8, 39.6, 57.5, 58.3 (x3), 67.5, 75.5, 82.1, 115.1, 154.2.
20. 1H NMR: δ 0.15 (s, 3H), 0.57 (dd, J = 14.8, 10.9 Hz, 1H), 1.07 (dd, J = 14.8, 3.6 Hz, 1H), 1.22 (t, J = 7.1 Hz, 6H), 1.4-1.8 (m, 4H), 1.86 (t, J = 2.3 Hz, 3H), 1.95-2.05 (m, 1H), 2.2-2.4 (m, 2H), 3.76 (q, J = 7.1 Hz, 4H), 4.05 (dd, J = 6.9, 1.3 Hz, 2H), 4.08 (q, J = 2.3 Hz, 2H), 5.37 (dq, J = 6.9, 2.6 Hz, 1H).
21. Reversibility of the hydropalladation in Pd-catalyzed cyclization-hydrosilylation of alkadiynes has not been established. However, reversible silylpalladation in the case of alkadienes under similar reaction conditions are discussed: X. Wang, H. Chakrapani, C. N. Stengone, R. A. Widenhoefer, J. Org. Chem. 2001, 66, 1755.