Molybdenum-catalyzed aromatic substitution with olefins and alcohols

Chemistry Letters

Volumn , Issue 9, 1997, Pages 851-852

  Shimizu, Isao ^a   Khien, Kuok Meng ^a   Nagatomo, Miki ^a   Nakajima, Takayuki ^a   Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038907538     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.851     Document Type: Article

References (15)

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2. I. Shimizu, T. Sakamoto, S. Kawaragi, Y. Maruyama, and A. Yamamoto, Chem. Lett., 1997, 137. Also for palladium-catalyzed processes using allylic alcohols, see; M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 69, 1065 (1996); Y. Tada, A. Satake, I. Shimizu, and A. Yamamoto, Chem. Lett., 1996, 1021.
3. I. Shimizu, T. Sakamoto, S. Kawaragi, Y. Maruyama, and A. Yamamoto, Chem. Lett., 1997, 137. Also for palladium-catalyzed processes using allylic alcohols, see; M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 69, 1065 (1996); Y. Tada, A. Satake, I. Shimizu, and A. Yamamoto, Chem. Lett., 1996, 1021.
4. I. Shimizu, T. Sakamoto, S. Kawaragi, Y. Maruyama, and A. Yamamoto, Chem. Lett., 1997, 137. Also for palladium-catalyzed processes using allylic alcohols, see; M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 69, 1065 (1996); Y. Tada, A. Satake, I. Shimizu, and A. Yamamoto, Chem. Lett., 1996, 1021.
5. 2 (Wakogel C-300) with 2% AcOEt in hexane gave 1-methoxyphenyl-1-phenylethane (99%). The ratio of o-, m-, and p-isomers (1: 0 : 4) was determined by GC (SE-30, 2 m).
6. H. Hasegawa and T. Higashimura, Polym. J., 13, 915 (1981); T. Yamato, C. Hideshima, G. K. S. Prakash, and G. A. Olah, J. Org. Chem., 56, 2089 (1991); T. Yamato, M. Fukumoto, N. Sakauc, T. Furusawa, and M. Tashiro, Synthesis, 1991, 699.
7. H. Hasegawa and T. Higashimura, Polym. J., 13, 915 (1981); T. Yamato, C. Hideshima, G. K. S. Prakash, and G. A. Olah, J. Org. Chem., 56, 2089 (1991); T. Yamato, M. Fukumoto, N. Sakauc, T. Furusawa, and M. Tashiro, Synthesis, 1991, 699.
8. H. Hasegawa and T. Higashimura, Polym. J., 13, 915 (1981); T. Yamato, C. Hideshima, G. K. S. Prakash, and G. A. Olah, J. Org. Chem., 56, 2089 (1991); T. Yamato, M. Fukumoto, N. Sakauc, T. Furusawa, and M. Tashiro, Synthesis, 1991, 699.
9. A. Kawada, S. Mitamura, and S. Kobayashi, Synlett, 1994, 545; A. Kawada, S. Mitamura, and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1993, 1157; T. Tsuchimoto, K. Tobita, T. Hiyama, and S. Fukuzawa, Synlett, 1996, 557.
10. A. Kawada, S. Mitamura, and S. Kobayashi, Synlett, 1994, 545; A. Kawada, S. Mitamura, and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1993, 1157; T. Tsuchimoto, K. Tobita, T. Hiyama, and S. Fukuzawa, Synlett, 1996, 557.
11. A. Kawada, S. Mitamura, and S. Kobayashi, Synlett, 1994, 545; A. Kawada, S. Mitamura, and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1993, 1157; T. Tsuchimoto, K. Tobita, T. Hiyama, and S. Fukuzawa, Synlett, 1996, 557.
12. Recently ruthenium-catalyzed aromatic substitution using olefins through C-H activation process has been reported. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
13. Recently ruthenium-catalyzed aromatic substitution using olefins through C-H activation process has been reported. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature, 366, 529 (1993); F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
14. Cationic cyclization of citral followed by reaction with methoxybenzene took place to give 2-(4-methoxyphenyl)-2-(4-methylphenyl)propane 4 in 44% yield. (equation presented)
15. S. Fukuzawa, T. Tsuchimoto, and T. Hiyama, J. Org. Chem., 62, 151 (1997).