Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3695-3698

  Itami, Kenichiro ^a   Ushiogi, Yousuke ^a   Nokami, Toshiki ^a   Ohashi, Youichi ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; FLUORESCENCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 7044284722     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048620i     Document Type: Article

References (22)

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2. Selected examples: (a) Kido, J.; Shionoya, H.; Nagai, K. Appl. Phys. Lett. 1995, 67, 2281. (b) Kim, J.-H.; Noh, S.; Kim, K.; Lim, S.-T.; Shin, D.-M. Synth. Met. 2001, 117, 227. (2) For previous synthesis of tetraphenylbutadiene, see: (a) Wittig, G.; von Lupin, F. Chem. Ber. 1928, 61, 1627. (b) Simes, B. E.; Rickborn, R.; Flournoy, J. M.; Berlman, I. B. J. Org. Chem. 1988, 53, 4613. (c) Feit, B.-A.; Buzhansky, L. J. Chem. Soc., Perkin Trans. 1 2000, 1777.
3. For previous synthesis of tetraphenylbutadiene, see: (a) Wittig, G.; von Lupin, F. Chem. Ber. 1928, 61, 1627.
4. For previous synthesis of tetraphenylbutadiene, see: (a) Wittig, G.; von Lupin, F. Chem. Ber. 1928, 61, 1627. (b) Simes, B. E.; Rickborn, R.; Flournoy, J. M.; Berlman, I. B. J. Org. Chem. 1988, 53, 4613. (c) Feit, B.-A.; Buzhansky, L. J. Chem. Soc., Perkin Trans. 1 2000, 1777.
5. For previous synthesis of tetraphenylbutadiene, see: (a) Wittig, G.; von Lupin, F. Chem. Ber. 1928, 61, 1627. (b) Simes, B. E.; Rickborn, R.; Flournoy, J. M.; Berlman, I. B. J. Org. Chem. 1988, 53, 4613. (c) Feit, B.-A.; Buzhansky, L. J. Chem. Soc., Perkin Trans. 1 2000, 1777.
6. Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2000, 122, 12013.
7. Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577.
8. Itami, K.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 5600.
9. Reviews: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693. (b) Yoshida, J.; Itami, K. J. Synth. Org. Chem. Jpn. 2001, 59, 1086.
10. Reviews: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693. (b) Yoshida, J.; Itami, K. J. Synth. Org. Chem. Jpn. 2001, 59, 1086.
11. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
12. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
13. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
14. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
15. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
16. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
17. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
18. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
19. Pd-mediated methods: (a) Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701. (b) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542. (c) Yamaguchi, S.; Ohno, S.; Tamao, K. Synlett 1997, 1199. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2003, 1510. Cu-mediated methods: (e) Yoshida, J.; Tamao, K.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1141. (f) Kang, S.-K.; Kim, T.-H.; Pyun, S.-J. J. Chem. Soc., Perkin Trans. 1 1997, 797. (g) Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985. Ag-mediated methods: (h) Mueller, R.; Dressler, M.; Dathe, C. J. Prakt. Chem. 1970, 312, 150. (i) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M. Tetrahedron Lett. 1979, 1137.
20. 4 (65%).
21. See Supporting Information for the preparation of 2 and 3.
22. Dimethyl(2-pyridyl)vinylsilane (1) is now commercially available from Tokyo Kasei Kogyo Co., Ltd (TCI). Catalog Number: D2935.