Synthesis of heterocyclic allenes via palladium-catalyzed hydride-transfer reaction of propargylic amines

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2357-2360

  Nakamura, Hiroyuki ^a   Onagi, Shinya ^a   Kamakura, Takaya ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BROMINE COMPOUNDS; CATALYSIS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALLENES; BROMIDES; HYDRIDE-TRANSFER REACTION; SONOGASHIRA COUPLING REACTION;

AROMATIC COMPOUNDS;

1,2 BIS[BIS(PENTAFLUOROPHENYL)PHOSPHINO]ETHANE; ALLENE DERIVATIVE; BROMINE DERIVATIVE; DIISOPROPYLAMINE; HETEROCYCLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE; PROPARGYLDIISOPROPYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HIGH TEMPERATURE PROCEDURES; SONOGASHIRA REACTION;

ALKENES; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; HYDROGEN; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; PARGYLINE; PROPYLAMINES;

EID: 15444379254     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479664     Document Type: Article

References (47)

1. (a) The Chemistry of Allenes; Landor, S. R. Ed.; Academic Press: London, 1982.
2. (b) Hoffmann-Roder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933.
3. (c) Modern Allene Chemistry; Krause, N., Hashmi, S., Eds.; Wiley-VCH: Weinheim, 2004.
4. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
5. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
6. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
7. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
8. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
9. For transition-metal-catalyzed reactions, see: (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (b) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. (c) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246. (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (e) Ahmed, M.; Amauld, T.; M. Barrett, A. G.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551. (f) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
10. For [2 + 2] cycloadditions, see: (a) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (b) Morimoto, T.; Horiguchi, T.; Yamada, K.; Tsutsumi, K.; Kurosawa, H.; Kakiuchi, K. Synthesis 2004, 753.
11. For [2 + 2] cycloadditions, see: (a) Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. J. Am. Chem. Soc. 1997, 119, 10869. (b) Morimoto, T.; Horiguchi, T.; Yamada, K.; Tsutsumi, K.; Kurosawa, H.; Kakiuchi, K. Synthesis 2004, 753.
12. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
13. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
14. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
15. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
16. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
17. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
18. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
19. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
20. For synthesis of heterocycles, see: (a) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1999, 64, 7312. (b) Grigg, R.; Sridharan, V.; Xu, L.-H. Chem. Commun. 1995, 1903. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (d) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581. (e) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285. (f) Brandasma, L.; Nedolya, N. Synthesis 2004, 735. (g) Regás, D.; Palenzuela, J. A. Synthesis 2004, 757. (h) Ishar, M. P.; Kapur, A.; Raj, T.; Girdhar, N. K.; Kaur, A. Synthesis 2004, 775. (i) Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280.
21. For polymer synthesis, see: Takagi, K.; Tomita, I.; Endo, T. Macromolecules 1997, 30, 7386.
22. (a) Allenes in Organic Synthesis; Coppola, G. M., Schuster, H. F., Eds.; Wiley: New York, 1984.
23. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. J. Am. Chem. Soc. 1990, 112, 8042.
24. Searles, S.; Li, Y.; Nassim, B.; Robert Lopes, M.-T.; Tran, P. T.; Crabbé, P. J. Chem. Soc., Perkin Trans. 1 1984, 747.
25. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
26. (a) Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089.
27. (b) Zimmermann, M.; Wibbeling, B.; Hoppe, D. Synthesis 2004, 765.
28. Fukuhara, K.; Okamoto, S.; Sato, F. Org. Lett. 2003, 5, 2145.
29. (a) Tanaka, K.; Otsubo, K.; Fuji, K. Synlett 1995, 993.
30. (b) Brummond, K. M.; Dingess, E. A.; Kent, J. L. J. Org. Chem. 1996, 61, 6096.
31. Delouvrie, B.; Lacote, E.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1996, 40, 3565.
32. (a) Tsuji, J.; Sugiura, T.; Yuhara, M.; Minami, I. Chem. Commun. 1986, 922.
33. (b) Tsuji, J.; Sugiura, T.; Minami, I. Synthesis 1987, 603.
34. (a) Badone, D.; Cardamome, R.; Guzzi, U. Tetrahedron Lett. 1994, 35, 5477.
35. (b) Huang, C.-W.; Shanmugasundaram, M.; Chang, H.-M.; Cheng, C.-H. Tetrahedron 2003, 59, 3635.
36. (a) Lee, K.; Seomon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901.
37. (b) Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042.
38. (a) Ma, S.; He, Q. Angew. Chem., Int. Ed. 2004, 43, 988.
39. (b) Ma, S.; Zhang, A. J. Org. Chem. 1998, 63, 9601.
40. Nakamura, H.; Kamakura, T.; Ishikura, M.; Biellmann, J.-F. J. Am. Chem. Soc. 2004, 126, 5958.
41. (a) Bleicher, L.; Cosford, N. D. P. Synlett 1995, 1115.
42. (b) Russo, O.; Alami, M.; Brion, J.-D.; Sicsic, S.; Berque-Bestel, I. Tetrahedron Lett. 2004, 45, 7069.
43. (a) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348.
44. (b) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7430.
45. (c) Saá, J. M.; Dopico, M.; Martorell, G.; García-Raso, A. J. Org. Chem. 1990, 55, 991.
46. (a) Krause, N.; Hoffmann-Röder, A. In Modern Allene Chemistry; Krause, N., Hashmi, S., Eds.; Wiley-VCH: Weinheim, 2004; p 997.
47. (b) Brummond, K. M.; Chen, H. In Modern Allene Chemistry; Krause, N., Hashmi, S., Eds.; Wiley-VCH: Weinheim, 2004; p 1041.