Highly efficient Pd(acac)2/TFA catalyzed head-to-tail dimerization of vinylarenes at room temperature

Tetrahedron Letters

Volumn 52, Issue 14, 2011, Pages 1569-1573

  Ma, Hengchang ^a   Sun, Qiangsheng ^a   Li, Wenfeng ^a   Wang, Jinxia ^a   Zhang, Zhe ^a   Yang, Yaoxia ^a   Lei, Ziqiang ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

Arenes; Catalysis; Dimerization; Palladium; Styrenes

Indexed keywords

DIMER; PALLADIUM; STYRENE DERIVATIVE; TRIFLUOROACETIC ACID; VINYL DERIVATIVE;

ARTICLE; ATOM; ATOM ECONOMIC REACTION; CATALYSIS; CATALYST; CHEMICAL REACTION; DIMERIZATION; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 79952362364     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.056     Document Type: Article

References (25)

1. T.-Y. Luh, M.-K. Leung, and K.-T. Wong Chem. Rev. 100 2000 3187
2. C.S. Chin, G. Won, D. Chong, M. Kim, and H. Lee Acc. Chem. Res. 35 2002 218
3. K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169
4. D. Prajapati, and M. Gohain Tetrahedron 60 2004 815
5. M. Shibasaki, E.M. Vogl, and T. Ohshima Adv. Synth. Catal. 346 2004 1533
6. C.-J. Li Chem. Rev. 105 2005 3095
7. T.V. RajanBabu Chem. Rev. 103 2003 2845
8. T. Kondo, D. Takagi, H. Tsujita, Y. Ura, K. Wada, and T.-A. Mitsudo Angew. Chem., Int. Ed. 46 2007 5958
9. Z.-Z. Jiang, and A. Sen J. Am. Chem. Soc. 112 1990 9655
10. G.W. Kabalka, G. Dong, and B. Venkataiah Tetrahedron Lett. 45 2004 2775
11. E. Hauptman, S. Sabo-Etienne, P.S. White, M. Brookhart, J.M. Garner, P.J. Fagan, and J.C. Calabreset J. Am. Chem. Soc. 116 1994 8038
12. J.-J. Peng, J.-Y. Li, H.-Y. Qiu, J.-X. Jiang, K.-Z. Jiang, J.-J. Mao, and G.-Q. Lai J. Mol. Catal. A: Chem. 255 2006 16
13. R.-B. Bedford, M. Betham, M.-E. Blake, A. Garcés, S.L. Millara, and S. Prasharc Tetrahedron 61 2005 9799
14. M. Rueping, B.J. Nachtsheim, and T. Scheidt Org. Lett. 8 2006 3717
15. J. Kischel, I. Jovel, K. Mertins, A. Zapf, and M. Beller Org. Lett. 8 2006 19
16. C.-Y. Yi, R.-M. Hua, and H.-X. Zeng Catal. Commun. 9 2008 85
17. G. Myagmarsuren, V.S. Tkach, F.K. Shmidt, M. Mohamad, and D.-S. Suslov J. Mol. Catal. A: Chem. 235 2005 154
18. F. Dawans Tetrahedron Lett. 12 1971 1943
19. T. Tsuchimoto, S. Kamiyama, R. Negoro, E. Shirakawa, and Y. Kawakami Chem. Commun. 2003 852
20. C.-C. Wang, P.-S. Lin, and C.-H. Cheng Tetrahedron Lett. 45 2004 6203
21. 2 (2.0 mL) in a round-bottomed flask was stirred at room temperature. Then, TFA (1.0 mmol) was added. The mixture was magnetically stirred at room temperature for 5 min until the complete consumption of styrene (observed by TLC). The mixture was subjected to silica gel column chromatography using a mixture eluent of ethyl acetate and petroleum ether (1:20 in volume). Compound 1b was isolated as viscous oil (99.8 mg, 0.48 mmol, 96%)
22. 3): δ = 21.28, 41.75, 115.10, 115.24, 115.30, 115.46, 127.50, 127.53, 127.60, 128.59, 128.67, 133.52, 133.56, 134.75, 134.77, 141.08, 141.12, 161.41 (J = 242 Hz), 162.06 (J = 245 Hz).
23. Z. Jiang, and A. Sen Organometallics 12 1993 1406
24. A. Sen, T.-W. Lai, and R.R. Thomas J. Organomet. Chem. 358 1988 567
25. C. Sui-Seng, L.F. Groux, and D. Zargarian Organometallics 25 2006 571