Zirconocene-catalyzed silylation of alkenes with chlorosilanes

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2653-2656

  Terao, Jun ^a   Torii, Kazushi ^a   Saito, Koyu ^a   Kambe, Nobuaki ^a   Baba, Akio ^a   Sonoda, Noboru ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

Alkenes; Silanes; Silylations; Zirconium

Indexed keywords

EID: 0032538468     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2653::AID-ANIE2653>3.0.CO;2-3     Document Type: Article

References (31)

1. a) The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1989;
2. b) L. Hevesi in Comprehensive Organic Functional Group Transformations, Vol. 2 (Ed.: S.V. Ley), Elsevier, Oxford, 1995, pp. 899-950;
3. c) D. A. Armitage in Comprehensive Organomettillic Chemistry II, Vol. 2 (Ed.: A. G. Davies), Elsevier, Oxford, 1995, pp. 1-44.
4. Recent reviews of transition metal catalyzed reactions of organosilanes: a) T. Hiyama, T. Kusumoto in Comprehensive Organic Synthesis. Vol. 8 (Ed.: I. Fleming), Pergamon, Oxford, 1991 , pp. 763-792; b) S. Murai, N. Chatani, J. Synth. Org. Chem. Jpn. 1993, 51, 421-433; c) C. A. Recatto, Aldrichimica Acta 1995, 28, 85-92; d) K. A. Horn, Chem. Rev. 1995, 95, 1317-1350.
5. Recent reviews of transition metal catalyzed reactions of organosilanes: a) T. Hiyama, T. Kusumoto in Comprehensive Organic Synthesis. Vol. 8 (Ed.: I. Fleming), Pergamon, Oxford, 1991 , pp. 763-792; b) S. Murai, N. Chatani, J. Synth. Org. Chem. Jpn. 1993, 51, 421-433; c) C. A. Recatto, Aldrichimica Acta 1995, 28, 85-92; d) K. A. Horn, Chem. Rev. 1995, 95, 1317-1350.
6. Recent reviews of transition metal catalyzed reactions of organosilanes: a) T. Hiyama, T. Kusumoto in Comprehensive Organic Synthesis. Vol. 8 (Ed.: I. Fleming), Pergamon, Oxford, 1991 , pp. 763-792; b) S. Murai, N. Chatani, J. Synth. Org. Chem. Jpn. 1993, 51, 421-433; c) C. A. Recatto, Aldrichimica Acta 1995, 28, 85-92; d) K. A. Horn, Chem. Rev. 1995, 95, 1317-1350.
7. Recent reviews of transition metal catalyzed reactions of organosilanes: a) T. Hiyama, T. Kusumoto in Comprehensive Organic Synthesis. Vol. 8 (Ed.: I. Fleming), Pergamon, Oxford, 1991 , pp. 763-792; b) S. Murai, N. Chatani, J. Synth. Org. Chem. Jpn. 1993, 51, 421-433; c) C. A. Recatto, Aldrichimica Acta 1995, 28, 85-92; d) K. A. Horn, Chem. Rev. 1995, 95, 1317-1350.
8. A. M. LaPointe, F. C. Rix, M. Brookhart, J. Am. Chem. Soc. 1997, 119., 906-917, and references therein.
9. a) H. Saso, W. Ando, Chem. Lett. 1988, 1567-1570;
10. b) H. Sakurai, T. Imai, Chem. Lett. 1975, 891-894.
11. N. Chatani, T. Hanafusa, J. Chem. Soc. Chem. Commun. 1985, 838-839.
12. A. Ogawa, H. Kuniyasu, M. Takeba, T. Ikeda, N. Sonoda, T. Hirao, J. Organomet. Chem., in press.
13. M. Hada, Y. Tanaka, M. Ito, M. Murakami, H. Amii, Y. Ito, H. Nakatsuji, J. Am. Chem. Soc. 1994, 116, 8754-8765, and references therein.
14. a) H. Yamashita, T. Kobayashi, T. Hayashi, M. Tanaka, Chem. Lett. 1991, 761-762;
15. b) N. Chatani, N. Amishiro, S. Murai, J. Am. Chem. Soc. 1991, 113, 7778-7780;
16. c) N. Chatani, N. Amishiro, T. Morii, T. Yamashita, S. Murai, J. Org. Chem. 1995, 60, 1834-1840.
17. H. Yamashita, M. Tanaka, M. Goto, Organometallics 1997, 16, 4696-4704, and references therein.
18. Recent reviews on the application of zirconocene complexes in syntheses: a) R. F. Jordan, Adv. Organomet. Chem. 1991, 52, 325-387; b) E. Negishi in Comprehensive Organic Synthesis Vol. 5, (Ed.: L. A. Paquette), Pergamon, Oxford, 1991, pp. 1163-1184; c) E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130.
19. Recent reviews on the application of zirconocene complexes in syntheses: a) R. F. Jordan, Adv. Organomet. Chem. 1991, 52, 325-387; b) E. Negishi in Comprehensive Organic Synthesis Vol. 5, (Ed.: L. A. Paquette), Pergamon, Oxford, 1991, pp. 1163-1184; c) E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130.
20. Recent reviews on the application of zirconocene complexes in syntheses: a) R. F. Jordan, Adv. Organomet. Chem. 1991, 52, 325-387; b) E. Negishi in Comprehensive Organic Synthesis Vol. 5, (Ed.: L. A. Paquette), Pergamon, Oxford, 1991, pp. 1163-1184; c) E. Negishi, T. Takahashi, Acc. Chem. Res. 1994, 27, 124-130.
21. 2Zr(butene)] formation, see b) V. K. Dioumaev, J. F. Harrod, Organometallics 1997, 16, 1452-1464; c) F. Soleil, R. Choukroun, J. Am. Chem. Soc. 1997, 119, 2938-2939.
22. 2Zr(butene)] formation, see b) V. K. Dioumaev, J. F. Harrod, Organometallics 1997, 16, 1452-1464; c) F. Soleil, R. Choukroun, J. Am. Chem. Soc. 1997, 119, 2938-2939.
23. 2Zr(butene)] formation, see b) V. K. Dioumaev, J. F. Harrod, Organometallics 1997, 16, 1452-1464; c) F. Soleil, R. Choukroun, J. Am. Chem. Soc. 1997, 119, 2938-2939.
24. 3): A signal for a terminal carbon atom at δ = 13.9 that appears as a triplet due to coupling with D (J= 1.9 Hz) is observed in addition to a singlet at δ = 14.2 for the other terminal carbon atom.
25. T. Takahashi, M. Hasegawa, N. Suzuki, M. Saburi, C. J. Rousset, P. E. Fanwick, E. Negishi, J. Am. Chem. Soc. 1991, 113, 8564-8566; M. R. Kesti, M. Abdulrahman, R. M. Waymouth, J. Organomet. Chem. 1991, 417, C12-C15; J. Y. Corey, X.-H. Zhu, Organometallics 1992, 11, 672-683; M. R. Kesti, R. M. Waymouth, Organometallics 1992, 11, 1095-1103.
26. T. Takahashi, M. Hasegawa, N. Suzuki, M. Saburi, C. J. Rousset, P. E. Fanwick, E. Negishi, J. Am. Chem. Soc. 1991, 113, 8564-8566; M. R. Kesti, M. Abdulrahman, R. M. Waymouth, J. Organomet. Chem. 1991, 417, C12-C15; J. Y. Corey, X.-H. Zhu, Organometallics 1992, 11, 672-683; M. R. Kesti, R. M. Waymouth, Organometallics 1992, 11, 1095-1103.
27. T. Takahashi, M. Hasegawa, N. Suzuki, M. Saburi, C. J. Rousset, P. E. Fanwick, E. Negishi, J. Am. Chem. Soc. 1991, 113, 8564-8566; M. R. Kesti, M. Abdulrahman, R. M. Waymouth, J. Organomet. Chem. 1991, 417, C12-C15; J. Y. Corey, X.-H. Zhu, Organometallics 1992, 11, 672-683; M. R. Kesti, R. M. Waymouth, Organometallics 1992, 11, 1095-1103.
28. T. Takahashi, M. Hasegawa, N. Suzuki, M. Saburi, C. J. Rousset, P. E. Fanwick, E. Negishi, J. Am. Chem. Soc. 1991, 113, 8564-8566; M. R. Kesti, M. Abdulrahman, R. M. Waymouth, J. Organomet. Chem. 1991, 417, C12-C15; J. Y. Corey, X.-H. Zhu, Organometallics 1992, 11, 672-683; M. R. Kesti, R. M. Waymouth, Organometallics 1992, 11, 1095-1103.
29. 5) has been reported; b) J. Arnold, M. P. Engeler, F. H. Elsner, R. H. Heyn, T. D. Tilley, Organometallics 1989, 8, 2284-2286.
30. 5) has been reported; b) J. Arnold, M. P. Engeler, F. H. Elsner, R. H. Heyn, T. D. Tilley, Organometallics 1989, 8, 2284-2286.
31. 2] with one equivalent of EtMgBr: T. Takahashi, N. Suzuki, M. Kageyama, Y. Nitto, M. Saburi, E. Negishi, Chem. Lett. 1991, 1579-1582.