Palladium-catalyzed highly regioselective [3 + 2] cycloaddition reactions of alkylidenecyclopropa[b]naphthalenes with alkenes or alkynes: An efficient synthesis of 1(3)-alkylidene-2,3-dihydro-1H-benzo[f]indenes and 1-alkylidene-1H-benzo[f]indenes

Organic Letters

Volumn 10, Issue 24, 2008, Pages 5537-5540

  Chen, Wanli ^b   Cao, Jian ^a   Huang, Xian ^a,c  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; INDENE DERIVATIVE; NAPHTHALENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; CYCLIZATION; INDENES; NAPHTHALENES; PALLADIUM;

EID: 60949088455     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8023083     Document Type: Article

References (33)

1. (a) Kim, D. H.; Lee, J. A.; Lee, B. Y.; Chung, Y. K. J. Organomet. Chem. 2005, 690, 1822.
2. (b) Carpino, L. A. Acc. Chem. Res. 1987, 20, 401.
3. (c) Mccurdy, C. R.; Bourdonnec, B. Le; Metzger, T. G.; Kouhen, R. E.; Zhang, Y.; Law, P. Y.; Portoghese, P. S. J. Med. Chem. 2002, 45, 2887.
4. (d) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267.
5. (a) Hsieh, J. C.; Cheng, C. H. Chem. Commun. 2000, 815.
6. (b) Oishi, E.; Taido, N.; Iwamoto, K.; Miyashita, A.; Higashino, T. Chem. Pharm. Bull. 1990, 38, 3268.
7. (a) Ghorai, S. K.; Hazra, N. K.; Mal, D. Tetrahedron Lett. 1998, 39, 689.
8. (b) Carpino, L. A.; Lin, Y. Z. J Org. Chem. 1990, 55, 247.
9. For reviews see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77.
10. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
11. (c) Binger, P.; Schmidt, T. In Houben-Weyl; Meijere, A. De, Eds.; Thieme: Stuttgart, 1997; Vol. E17c, p 2217.
12. (d) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 217.
13. (e) Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
14. (a) Yang, Y.; Huang, X. J. Org. Chem. 2008, 73, 4702.
15. (b) Chen, W.; Su, C.; Huang, X. Synlett 2006, 1446.
16. (c) Huang, X.; Zhou, H.; Chen, W. J. Org. Chem. 2004, 69, 839.
17. (d) Zhou, H.; Huang, X.; Chen, W. J. Org. Chem. 2004, 69, 5471.
18. (e) Chen, W.; Huang, X.; Zhou, H.; Ren, L. Synthesis 2006, 609.
19. For synthesis of MCPs, see: (f) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
20. For recent reviews, see: (g) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
21. (h) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
22. (a) Halton, B. Chem. Rev. 2003, 103, 1327.
23. (b) Halton, B. Chem. Rev. 1989, 89, 1161.
24. (c) Billups, W. E.; Rodin, W. A.; Haley, M. M. Tetrahedron 1988, 44, 1305.
25. Stang, P. J.; Song, L.; Lu, Q.; Halton, B. Organometallics 1990, 9, 2149.
26. Halton, B.; Randall, C. J.; Gainsford, G. J.; Stang, P. J. J. Am. Chem. Soc. 1986, 108, 5949.
27. At present, the role for the LiCl additive is not clear. We think this may have some salt effect or act as the ligand in the reaction. For selected papers of the LiCl additive, please see: (a) Ma, S.; Zhang, J. Angew. Chem., Int. Ed. 2003, 42, 184.
28. (b) Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc. 2004, 126, 9645.
29. (c) Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 82.
30. (d) Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775.
31. (e) Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Ran, X. Organometallics 2001, 20, 3724.
32. int = 0.0500), 12207 reflections collected; refinement method, full-matrix least-squares refinement on F2; goodness-of-fit on F2 = 0.919; final R indices [I > 2σ(I)] R1 = 0.0577, wR2 = 0.1361.
33. Suzuki, T.; Fujimoto, H. Inorg. Chem. 2000, 39, 1113.