Synthesis of indenes via palladium-catalyzed carboannulation of diethyl 2-(2-(1-alkynyl)phenyl)malonate and organic halides

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3325-3327

  Guo, Li Na ^a   Duan, Xin Hua ^a   Bi, Hai Peng ^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

HALIDE MINERALS; SYNTHESIS (CHEMICAL);

CARBOANNULATION; DIETHYL 2-(2-(1-ALKYNYL)PHENYL)MALONATE; ORGANIC HALIDES;

AROMATIC COMPOUNDS;

ALKENYL GROUP; BENZYL DERIVATIVE; MALONIC ACID DERIVATIVE; ORGANOHALOGEN DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ANNULATION REACTION; ARTICLE; CARBOANNULATION REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 33645783912     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0601361     Document Type: Article

References (29)

1. (a) Xi, Z.; Guo, R.; Mito, S.; Yan, H.; Kanno, K.-i.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2003, 68, 1252 and references therein.
2. (b) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 7280.
3. (c) Lautens, M.; Marquardt, T. J. Org. Chem. 2004, 69. 4607.
4. (d) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 4781.
5. (a) Prough, J.; Alberts, A.; Deanna, A.; Gilfillian, J.; Huff, R.; Smith, J.; Wiggins, J. J. Med. Chem. 1990, 33, 758.
6. (b) Ikeda, S.; Chatani, N.; Kajikawa, Y.; Ohe, K.; Murai, S. J. Org. Chem. 1992, 57, 2.
7. (c) Becker, C.; McLaughlin, M. Synlett 1991, 642.
8. Miller, W.; Pittman, C. J. Org. Chem. 1974, 39, 1955.
9. Yoshida, H.; Kato, M.; Ogata, T. J. Org. Chem. 1985, 50, 1145.
10. (a) Nakamura, I.; Bajracharya, G. B.; Wu, H.; Oishi, K.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 15423.
11. (b) Nakamura, I.; Bajracharya, G. B.; Mizushima, Y.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 4328.
12. Zhang, D.; Yum, E. K.; Liu, Z.; Larock, R. C. Org. Lett. 2005, 7, 4963.
13. For reviews, see: (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
14. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
15. For some recent examples, see: (c) Harmata, M.; Rayanil, K.-o.; Gomes, M. G.; Zheng, P.; Calkins, N. L.; Kim, S.-Y.; Fan, Y.; Bumbu, V.; Lee, D. R.; Wacharasindhu, S.; Hong, X. Org. Lett. 2005, 7, 143.
16. (d) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553.
17. (e) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86.
18. (f) Zhang, H.; Larock, R. C. Org. Lett. 2001, 3, 3083.
19. (g) Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 7048.
20. (h) Kundu, N. G.; Khan, M. W. Tetrahedron. 2000, 56, 4777.
21. For reviews, see: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
22. (b) Cacchi, S. J. Organomet. Chem. 1999, 576, 42 and references therein.
23. For some recent examples, see: (c) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2003, 5, 2441.
24. (d) Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035.
25. (e) Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920.
26. (f) Wei, L.-M.; Lin, C.-F.; Wu, M.-J. Tetrahedron Lett. 2000, 41, 1215.
27. Duan, X.-h.; Liu, X.-y.; Guo, L.-n.; Liao, M.-c.; Liu, W.-M.; Liang, Y.-m. J. Org. Chem. 2005, 70, 6980.
28. Similar results were observed in a Pd-catalyzed coupling reaction, see: ref 8d and ref 8e.
29. A similar result was observed in a Pd-catalyzed coupling/cyclization reaction, see: Arcadi, A.; Cacchi, S.; Larock, R. C.; Marinelli, F. Tetrahedron Lett. 1993, 34, 2813.