Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3313-3316

  Du, Xiaoli ^a   Suguro, Masahiro ^a   Hirabayashi, Kazunori ^a   Mori, Atsunori ^a   Nishikata, Takashi ^b   Hagiwara, Nobuhito ^b   Kawata, Kentaro ^b   Okeda, Takeaki ^b   Wang, Hui Feng ^b   Fugami, Keigo ^b   Kosugi, Masanori ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 18044402758     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016529y     Document Type: Article

References (25)

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2. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
3. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345.
4. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 1996.
5. (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
6. (b) Hirabayashi, K.; Kondo, T.; Toriyama, F.; Nishihara, Y.; Mori, A. Bull. Chem. Soc. Jpn. 2000, 73, 749.
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8. (a) Oda, H.; Morishita, M.; Fugami, K.; Sano, H.; Kosugi, M. Chem. Lett. 1996, 811.
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13. (a) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.
14. (b) Rhodium-catalyzed MH-type reaction of boronic acid: Lautens, M.; Roy, Amélie, Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. See also:
15. (c) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
16. (d) Karabelas, K.; Hallberg, A. J. Org. Chem. 1988, 53, 4909.
17. 4 with AgOAc in acetic acid was also shown by Uemura: Cho, C. S.; Itotani, K.; Uemura, S. J. Organomet. Chem. 1993, 443, 253.
18. Rossi, B.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523.
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21. (c) Yagyu, T.; Osakada, K.; Brookhart, M. Organometallics 2000, 19, 2125 and references therein.
22. (d) Takahashi, T.; Seki, S.; Kotora, M. Jpn. Kokai Tokkyo Koho JP 08301792 A2 19 Nov 1996 Heisei; Chem. Abstr. 1997, 126, 89089.
23. Bailey, P. M.; Mann, B. E.; Brown, I. D.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1976, 238.
24. (a) A related reaction catalyzed by Pd(0) is reported to proceed via a formation of palladacyclopentadiene intermediate: Shirakawa, E.; Yoshida, H.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 4290.
25. (b) A fulvene formation via nickelacyclopentadiene: Iyoda, M.; Mizusuna, A.; Oda, M. Chem. Lett. 1988, 149.