New insight into Ni(II)-catalyzed cyclization reactions of propargylic compounds with soft nucleophiles: Novel indenes formation

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3837-3841

  Gou, Fa Rong ^a   Bi, Hai Peng ^a   Guo, Li Na ^a   Guan, Zheng Hui ^a   Liu, Xue Yuan ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CYCLIZATION; NICKEL; NUCLEOPHILES; REACTION KINETICS;

CARBOANNULATION REACTIONS; INDENE DERIVATIVES; PROPARGYLIC COMPOUNDS; REACTION CONDITIONS;

AROMATIC COMPOUNDS;

GRIGNARD REAGENT; INDENE DERIVATIVE; NICKEL; ORGANIC COMPOUND; PROPARGYLIC ACETATE; PROPARGYLIC ALCOHOL; PROPARGYLIC CARBONATE; PROPARGYLIC COMPOUND;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION OPTIMIZATION; REPRODUCIBILITY; STEREOSPECIFICITY; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; INDENES; MOLECULAR STRUCTURE; NICKEL; STEREOISOMERISM;

EID: 43449093757     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800155a     Document Type: Article

References (43)

1. (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. T. Chem. Rev. 1996, 96, 935.
2. (b) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265.
3. For reviews on palladium-catalyzed reactions of propargylic compounds. see:(a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
4. (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225.
5. (c) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
6. Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 6053.
7. For reviews see:(a) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
8. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539.
9. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
10. (d) Mortreux, A. In Transition Metal Catalysed Reactions: Murahashi, S.-I., Davies, S. G., Eds.; Blackwell Science Ltd.: London, 1999; pp 159-167.
11. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467.
12. (f) Montgomery, J.; Amarasinghe, K. K. D.; Chowdhury, S. K.; Oblinger, E.; Seo, J.; Savchenko, A. V. Pure Appl. Chem. 2002, 74, 129.
13. (g) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120.
14. (a) Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Chem. Soc., Chem. Commun. 1995, 1863.
15. (b) Alvarez, E.; Cuvigny, T.; Julia, M. J. Organomet. Chem. 1988, 339, 199.
16. For leading and recent references, see:(a) Chuit, C.; Felkin, H.; Frajerman, C.; Roussi, G.; Swierczewski, G. J. Chem. Soc., Chem. Commun. 1968, 1604.
17. (b) Cherest, M.; Felkin, H.; Umpleby, J. O. J. Chem. Soc., Chem. Commun. 1981, 681.
18. (c) Consiglio, G.; Morandini, F.; Piccolo, O. J. Am. Chem. Soc. 1981, 103, 1846.
19. (d) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043.
20. (e) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789.
21. (f) Kang, S. K.; Cho, D. G.; Park, C. H.; Namkoong, E. Y.; Shin, J. S. Synth. Commun. 1995, 25, 1659.
22. Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185.
23. (a) Guo, L.-N.; Duan, X.-H.; Bi. H.-P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2006, 71, 3325.
24. (b) Duan, X.-H.; Guo, L.-N.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2006, 8, 3053.
25. (c) Duan, X.-H.; Guo, L.-N.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2006, 8, 5777.
26. (d) Guo, L.-N.; Duan, X.-H.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2007, 72, 1538.
27. (e) Bi, H.-P.; Liu, X.-Y.; Gou, F.-R.; Guo, L.-N.; Duan, X.-H.; Shu, X.-Z.; Liang, Y.-M. Angew. Chem., Int. Ed. 2007, 46, 7068.
28. (f) Bi, H.-P.; Liu, X.-Y.; Gou, F.-R.; Guo, L.-N.; Duan, X.-H.; Liang, Y.-M. Org. Lett. 2007, 9, 3527.
29. (a) Zhang, D. H.; Liu, Z. J.; Yum, E. K.; Larock, R. C. J. Org. Chem. 1995, 60, 3270.
30. (b) Monteiro, N.; Gore, J.; Balme, G. Tetrahedron 1992, 48, 10103.
31. (c) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 1990, 126, 4526.
32. (d) Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350.
33. (a) Landor, S. R., Ed. The Chemistry of Allenes; Academic Press: London, 1982.
34. (b) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2002, 41, 2933.
35. (c) Krause, N., Hashmi, A. S. K., Eds. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004.
36. (a) Jarvi, E. T.; McCarthy, J. R. Nucleoside Nucleotide 1994, 13, 585.
37. (b) Dauvergne, J.; Burger, A.; Biellmann, J.-F. Nucleoside Nucleotide 2001, 20, 1775.
38. (a) Schuster, H. F., Coppola, G. M., Eds. Allenes in Organic Synthesis; Wiley: New York, 1984.
39. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. J. Am. Chem. Soc. 1990, 112, 8042.
40. (a) Arzoumanian, H.; Cochini, F.; Nuel, D.; Petrignani, J. F.; Rosas, N. Organometallics 1992, 11, 493.
41. (b) Arzoumanian, H.; Cochini, F.; Nuel, D.; Petrignani, J. F.; Rosas, N. Organometallics 1993, 12, 1871.
42. (a) Paste, D. J.; Chou, S.-K.; Waterhouse, A.; Shults, R. H.; Hennion, G. F. J. Org. Chem. 1978, 43, 1385.
43. (b) Paste, D. J.; Chou, S.-K.; Fritzen, E.; Shults, R. H.; Waterhouse, A.; Hennion, G. F. J. Org. Chem. 1978, 43, 1389.