In(OTf)3-catalyzed highly chemo- and regioselective head-to-tail heterodimerization of vinylarenes with 1,1-diarylethenes

Chemistry - A European Journal

Volumn 17, Issue 30, 2011, Pages 8290-8293

  Dai, Jing ^a   Wu, Jinlong ^a   Zhao, Guanglian ^a   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

alkenes; C H activation; carbocations; hydroalkenylation; Lewis acids

Indexed keywords

ACTIVATION ANALYSIS; OLEFINS; STYRENE;

C-H ACTIVATION; CARBOCATIONS; CHEMO-AND REGIOSELECTIVITIES; CYCLODIMERIZATION; HETERODIMERIZATION; HYDROALKENYLATION; LEWIS ACID; REGIO-SELECTIVE;

REGIOSELECTIVITY;

EID: 79960313157     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101190     Document Type: Article

References (47)

1. For reviews, see S. M. Pillai, M. Ravindranathan, S. Sivaram, Chem. Rev. 1986, 86, 353-399
2. J. Skupinska, Chem. Rev. 1991, 91, 613-648
3. C. Janiak, Coord. Chem. Rev. 2006, 250, 66-94, and references therein; for reviews on Ni-catalyzed processes, see
4. B. Bogdanović, Adv. Organomet. Chem. 1979, 17, 105-140
5. A. C. L. Su, Adv. Organomet. Chem. 1979, 17, 269-318
6. G. Wilke, Angew. Chem. 1988, 100, 189-211
7. Angew. Chem. Int. Ed. Engl. 1988, 27, 185-206
8. W. Keim, Angew. Chem. 1990, 102, 251-260
9. Angew. Chem. Int. Ed. Engl. 1990, 29, 235-244
10. Y. Chauvin, H. Oliver, in Applied Homogeneous Catalysis with Organometallic Compounds, Vol.1 (Eds.:, B. Cornils, W.A. Herrmann,), Wiley-VCH, New York, 1996, p. 258-268.
11. M. G. Barlow, M. J. Bryant, R. N. Haszeldine, A. G. Mackie, J. Organomet. Chem. 1970, 21, 215-226.
12. 3/Zn, see
13. 2/arenediazonium salts in ionic liquids, see
14. 3N, see
15. 2, see
16. 2/TFA, see
17. H. Ma, Q. Sun, W. Li, J. Wang, Z. Zhang, Y. Yang, Z. Lei, Tetrahedron Lett. 2011, 52, 1569-1573; see also the Supporting Information for a complete list of references.
18. For the tail-to-tail homodimerization of vinylarenes by using palladium complexes, see G. Wu, A. L. Rheingold, R. F. Heck, Organometallics 1987, 6, 2386-2391
19. 2, see
20. R. N. Das, K. Sarma, M. G. Pathak, A. Goswami, Synlett 2010, 2908-2912; for the use of [(IPr)NiH]OTf, see
21. C.-Y. Ho, L. He, Angew. Chem. 2010, 122, 9368-9372
22. Angew. Chem. Int. Ed. 2010, 49, 9182-9186.
23. 2], see:, T. Kondo, D. Takagi, H. Tsujita, Y. Ura, K. Wada, T. Mitsudo, Angew. Chem. 2007, 119, 6062-6065
24. Angew. Chem. Int. Ed. 2007, 46, 5958-5961.
25. For the cyclodimerization of styrene, see A. R. Taylor, G. W. Keen, E. J. Eisenbraun, J. Org. Chem. 1977, 42, 3477-3480
26. E. Alesso, R. Torviso, M. Erlich, L. Finkielsztein, B. Lantaño, G. Moltrasio, J. Aguirre, P. Vázquez, L. Pizzio, C. Cáceres, M. Blanco, H. Thomas, Synth. Commun. 2002, 32, 3803-3812.
27. For a review, see:, C. Wang, Z. Xi, Chem. Soc. Rev. 2007, 36, 1395-1406.
28. 3, see:, M. Tobisu, I. Hyodo, M. Onoe, N. Chatani, Chem. Commun. 2008, 6013-6015.
29. For the cyclodimerization of 1,1-diphenylethene by using Lewis acids, see R. Wolovsky, N. Maoz, J. Org. Chem. 1973, 38, 4040-4044
30. M. Higashimura, K. Imamura, Y. Yokogawa, T. Sakakibara, Chem. Lett. 2004, 33, 728-729
31. C. Peppe, E. S. Lang, F. MolinosdeAndrade, L. BorgesdeCastro, Synlett 2004, 1723-1726
32. H.-B. Sun, B. Li, R. Hua, Y. Yin, Eur. J. Org. Chem. 2006, 4231-4236.
33. For the cyclodimerization of 1,1-diarylethenes by using aminium hexachloroantimonates, see F. Ciminale, L. Lopez, G. Mele, Tetrahedron 1994, 50, 12685-12696
34. F. Ciminale, L. Lopez, V. Paradiso, A. Nacci, Tetrahedron 1996, 52, 13971-13980
35. F. Ciminale, L. Lopez, G. M. Farinola, S. Sportelli, A. Nacci, Eur. J. Org. Chem. 2002, 3850-3854; for an example of the intermolecular hydroalkenylation of 1,1-diphenylethene with vinylferrocene, see
36. G. A. Mirafzal, N. L. Bauld, Organometallics 1991, 10, 2506-2508.
37. For reviews on the well-established Ni-catalyzed hydrovinylation reaction, see T. V. RajanBabu, Chem. Rev. 2003, 103, 2845-2860
38. T. V. RajanBabu, Synlett 2009, 853-885; for an asymmetric version, see
39. W.-J. Shi, Q. Zhang, J.-H. Xie, S.-F. Zhu, G.-H. Hou, Q.-L. Zhou, J. Am. Chem. Soc. 2006, 128, 2780-2781
40. A. Zhang, T. V. RajanBabu, J. Am. Chem. Soc. 2006, 128, 5620-5621.
41. 2, see
42. 2], see
43. 2], see
44. H. Tsujita, Y. Ura, S. Matsuki, K. Wada, T. Mitsudo, T. Kondo, Angew. Chem. 2007, 119, 5252-5255
45. Angew. Chem. Int. Ed. 2007, 46, 5160-5163; for a highlight, see
46. L. J. Gooßen, N. Rodríguez, Angew. Chem. 2007, 119, 7688-7690
47. Angew. Chem. Int. Ed. 2007, 46, 7544-7546.