Palladium-catalyzed controlled carbopalladation of benzyne

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7280-7286

  Yoshikawa, Eiji ^a   Radhakrishnan, K V ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; INDENE DERIVATIVE; PALLADIUM; PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; REACTION ANALYSIS;

EID: 0034596283     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001205a     Document Type: Article

References (36)

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27. A new hypervalent iodine-benzyne precursor, (phenyl)[2-(trimethylsilyl)phenyl]iodonium triflate, was reported recently. (a) Kitamura, T.; Yamane, M. J. Chem. Soc., Chem. Commun. 1995, 983-984. (b) Kitamura, T.; Yamane, M.; Inoue, K.; Todaka, M.; Fukatsu, N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674-11679. The use of this benzyne precursor in our Pd reactions gave a complex mixture of products.
28. 2.
29. 3CN/THF (1/1). Then, again CsF (2.0 equiv) was added and the resulting mixture was stirred at 60°C for 1 day.
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31. For transition metal mediated cyclotrimerization of alkynes which produces vinylcyclopentadienes, see: (a) Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2285-2294. (b) Inoue, Y.; Itoh, Y.; Hashimoto, H. Chem. Lett. 1978, 633-634. (c) Inoue, Y.; Itoh, Y.; Haruo, K.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329-3333. (d) Kong, K.-C.; Cheng, C.-H. J. Chem. Soc., Chem. Commun. 1991, 423-424. (e) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946.
32. For transition metal mediated cyclotrimerization of alkynes which produces vinylcyclopentadienes, see: (a) Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2285-2294. (b) Inoue, Y.; Itoh, Y.; Hashimoto, H. Chem. Lett. 1978, 633-634. (c) Inoue, Y.; Itoh, Y.; Haruo, K.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329-3333. (d) Kong, K.-C.; Cheng, C.-H. J. Chem. Soc., Chem. Commun. 1991, 423-424. (e) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946.
33. For transition metal mediated cyclotrimerization of alkynes which produces vinylcyclopentadienes, see: (a) Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2285-2294. (b) Inoue, Y.; Itoh, Y.; Hashimoto, H. Chem. Lett. 1978, 633-634. (c) Inoue, Y.; Itoh, Y.; Haruo, K.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329-3333. (d) Kong, K.-C.; Cheng, C.-H. J. Chem. Soc., Chem. Commun. 1991, 423-424. (e) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946.
34. For transition metal mediated cyclotrimerization of alkynes which produces vinylcyclopentadienes, see: (a) Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2285-2294. (b) Inoue, Y.; Itoh, Y.; Hashimoto, H. Chem. Lett. 1978, 633-634. (c) Inoue, Y.; Itoh, Y.; Haruo, K.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329-3333. (d) Kong, K.-C.; Cheng, C.-H. J. Chem. Soc., Chem. Commun. 1991, 423-424. (e) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946.
35. It is reasonable to assume that the isomer ratio is not influenced strongly by the stereoelectronic effect of the Me group at the C-4 position of the methylbenzyne 6b (see eq 10).
36. Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101-2108.