Catalytic dehydrative allylation of alcohols

Angewandte Chemie - International Edition

Volumn 44, Issue 11, 2005, Pages 1730-1732

  Saburi, Hajime ^a   Tanaka, Shinji ^a   Kitamura, Masato ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Allyl ethers; Allylation; Homogeneous catalysis; Quinolinecarboxylic acid; Ruthenium

Indexed keywords

ACTIVATION ANALYSIS; CARBOXYLIC ACIDS; CATALYSIS; DEHYDRATION; ETHERS; SOLVENTS; SYNTHESIS (CHEMICAL);

ALLYL ETHERS; CATALYTIC DEHYDRATIVE ALLYLATION; CHEMOSELECTIVE PROTECTION;

ALCOHOLS;

EID: 17044365831     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462513     Document Type: Article

References (36)

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8. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
9. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
10. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
11. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
12. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
13. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
14. Pd: a) R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412-3413; b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111-147; c) R. C. Larock, N. H. Lee, Tetrahedron Lett. 1991, 32, 6315-6318; d) R. Lakhmiri, P. Lhoste, D. Sinou, Tetrahedron Lett. 1989, 30, 4669-4672; e) J. Muzart, J.-P. Genêt, A. Denis, J. Organomet. Chem. 1987, 326, C23-C28; f) I. Minami, I. Shimizu, J. Tsuji, J. Organomet. Chem. 1985, 296, 269-280; g) F. Güibe, Y. S. M'leux, Tetrahedron Lett. 1981, 22, 3591-3594; h) K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 1972, 45, 230-236; Ir: i) H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 3474-3477.
15. For a recent example of Pd-catalyzed allylation of metal alkoxides with allyl esters, see: H. Kim, C. Lee, Org. Lett. 2002, 4, 4369-4371.
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18. Pd: Y. Kayaki, T. Koda, T. Ikariya, J. Org. Chem. 2004, 69, 2595-2597; Ru: R. C. van der Drift, M. Vailati, E. Bouwman, E. Drent, J. Mol. Catal. A 2000, 159, 163-177; Ni: H. Bricout, J.-F. Carpentier, A. Mortreux, J. Mol. Catal. A 1998, 136, 243-251.
19. Pd: Y. Kayaki, T. Koda, T. Ikariya, J. Org. Chem. 2004, 69, 2595-2597; Ru: R. C. van der Drift, M. Vailati, E. Bouwman, E. Drent, J. Mol. Catal. A 2000, 159, 163-177; Ni: H. Bricout, J.-F. Carpentier, A. Mortreux, J. Mol. Catal. A 1998, 136, 243-251.
20. Pd: Y. Kayaki, T. Koda, T. Ikariya, J. Org. Chem. 2004, 69, 2595-2597; Ru: R. C. van der Drift, M. Vailati, E. Bouwman, E. Drent, J. Mol. Catal. A 2000, 159, 163-177; Ni: H. Bricout, J.-F. Carpentier, A. Mortreux, J. Mol. Catal. A 1998, 136, 243-251.
21. For acid-catalyzed direct allylation, see: a) E. Moffett, J. Am. Chem. Soc. 1934, 56, 2009; b) M. J.-B. Senderens, Compt. Rend. 1925, 181, 698-701; for oxymetalation-dehydroxymetalation usingCu, Pd, and Hg, see: c) W. Oguchi, H. Uchida, WO Patent 03/106024, 2003; d) C. M. Dumlao, J. W. Francis, P. M. Henry, Organometallics 1991, 10, 1400-1405; e) W. H. Watanabe, L. E. Conlon, J. C. H. Hwa, J. Org. Chem. 1958, 23, 1666-1668.
22. For acid-catalyzed direct allylation, see: a) E. Moffett, J. Am. Chem. Soc. 1934, 56, 2009; b) M. J.-B. Senderens, Compt. Rend. 1925, 181, 698-701; for oxymetalation-dehydroxymetalation usingCu, Pd, and Hg, see: c) W. Oguchi, H. Uchida, WO Patent 03/106024, 2003; d) C. M. Dumlao, J. W. Francis, P. M. Henry, Organometallics 1991, 10, 1400-1405; e) W. H. Watanabe, L. E. Conlon, J. C. H. Hwa, J. Org. Chem. 1958, 23, 1666-1668.
23. For acid-catalyzed direct allylation, see: a) E. Moffett, J. Am. Chem. Soc. 1934, 56, 2009; b) M. J.-B. Senderens, Compt. Rend. 1925, 181, 698-701; for oxymetalation-dehydroxymetalation usingCu, Pd, and Hg, see: c) W. Oguchi, H. Uchida, WO Patent 03/106024, 2003; d) C. M. Dumlao, J. W. Francis, P. M. Henry, Organometallics 1991, 10, 1400-1405; e) W. H. Watanabe, L. E. Conlon, J. C. H. Hwa, J. Org. Chem. 1958, 23, 1666-1668.
24. For acid-catalyzed direct allylation, see: a) E. Moffett, J. Am. Chem. Soc. 1934, 56, 2009; b) M. J.-B. Senderens, Compt. Rend. 1925, 181, 698-701; for oxymetalation-dehydroxymetalation usingCu, Pd, and Hg, see: c) W. Oguchi, H. Uchida, WO Patent 03/106024, 2003; d) C. M. Dumlao, J. W. Francis, P. M. Henry, Organometallics 1991, 10, 1400-1405; e) W. H. Watanabe, L. E. Conlon, J. C. H. Hwa, J. Org. Chem. 1958, 23, 1666-1668.
25. For acid-catalyzed direct allylation, see: a) E. Moffett, J. Am. Chem. Soc. 1934, 56, 2009; b) M. J.-B. Senderens, Compt. Rend. 1925, 181, 698-701; for oxymetalation-dehydroxymetalation usingCu, Pd, and Hg, see: c) W. Oguchi, H. Uchida, WO Patent 03/106024, 2003; d) C. M. Dumlao, J. W. Francis, P. M. Henry, Organometallics 1991, 10, 1400-1405; e) W. H. Watanabe, L. E. Conlon, J. C. H. Hwa, J. Org. Chem. 1958, 23, 1666-1668.
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35. The ratio of 3a, 2, and diallyl ether after 30 minutes was approximately 40:20:20.
36. 3, Z = 2, R = 0.136, Rw = 0.163. CCDC 251818 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.