New protocol for the siteselective alkylation and vinylation of aromatic compounds. Catalyst-specific reactions

Chemistry Letters

Volumn , Issue 10, 1998, Pages 1053-1054

  Kakiuchi, Fumitoshi ^a   Sato, Taisuke ^a   Tsujimoto, Takuya ^a   Yamauchi, Masakazu ^a   Chatani, Naoto ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032257316     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1053     Document Type: Article

References (20)

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5. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
6. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
7. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
8. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
9. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
10. For representative examples, see: regioselective cross-coupling, T. Hayashi, M. Konishi, K. Yokota, and M. Kumada, J. Chem. Soc., Chem. Commun., 1981, 313; regioselective hydroformylation, T. Fuchikami and I. Ojima, J. Am. Chem. Soc., 104, 3527 (1982); regioselective alkylation of allylic compounds, J. Tsuji, I. Shimizu, I. Minami, and Y. Ohashi, Tetrahedron Lett., 23, 4809 (1982), B. M. Trost and M.-H. Hung, J. Am. Chem. Soc., 106, 6837 (1984); enantioselective hydrogenation, H. Takaya, T. Ohta, N. Sayo, H. Kumobayashi, S. Akutagawa, S.-I. Inoue, I. Kasahara, and R. Noyori, J. Am. Chem. Soc., 109, 1596 (1987); chemoselective hydrogenation of conjugated enones, J. M. Grosselin, C. Mercier, G. Allmang, and F. Grass, Organometallics, 10, 2126 (1991).
11. a) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature(London), 366, 529 (1993).
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13. c) F. Kakiuchi, Y. Yamamoto, N. Chatani, and S. Murai, Chem. Lett., 1995, 681.
14. d) F. Kakiuchi, M. Yamauchi, N. Chatani, and S. Murai, Chem. Lett., 1996, 111.
15. e) M. Sonoda, F. Kakiuchi, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 70, 3117 (1997).
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17. For the catalytic reactions, two equivalents of an olefin or an acetylene were used, unless otherwise noted.
18. The C-H bond at 2-position. i.e., position ortho to both of the acetyl and the imino groups, does not add to an olefin due to the steric congestion around this position.
19. 3-catalyzed hydrogenation of olefins, rhodium intermediates having two phosphine ligands have been proposed, see: J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, "Principles and Applications of Organotransition Metal Chemistry," University Science Books, California (1987), pp 531-535; G. O. Spessard and G. L. Miessler, "Organometallic Chemistry," Prentice-Hall, New Jersey (1997), pp 277-281.
20. 3-catalyzed hydrogenation of olefins, rhodium intermediates having two phosphine ligands have been proposed, see: J. P. Collman, L. S. Hegedus, J. R. Norton, and R. G. Finke, "Principles and Applications of Organotransition Metal Chemistry," University Science Books, California (1987), pp 531-535; G. O. Spessard and G. L. Miessler, "Organometallic Chemistry," Prentice-Hall, New Jersey (1997), pp 277-281.