Arylation of styrenes with aryliron complexes [CpFe(CO)2Ar]

Organometallics

Volumn 29, Issue 11, 2010, Pages 2634-2636

  Yasuda, Shigeo ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS;

AROMATIC HYDROCARBONS; XYLENE;

STYRENE;

EID: 77953220924     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1001952     Document Type: Article

References (40)

1. Pearson, A. J. Iron Compounds in Organic Synthesis; Academic Press: London, 1994.
2. Pearson, A. J. Pure Appl. Chem. 1983, 55, 1767-1779
3. 2R] has been summarized: Kerber, R. C. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Elsevier: Oxford, U.K., 1995; Vol. 7, Chapter 2.
4. Reaction with diphenylacetylene yielding indenone derivatives: Butler, I. R.; Cullen, W. R.; Lindsell, W. E.; Preston, P. N.; Rettig, S. J. J. Chem. Soc., Chem. Commun. 1987, 439-441
5. Insertion of unsaturated bonds into aryl-iron bonds: Severson, R. G.; Leung, T. W.; Wojcicki, A. Inorg. Chem. 1980, 19, 915-923
6. Su, S. R.; Wojcicki, A. Inorg. Chem. 1975, 14, 89-98
7. Jacobson, S. E.; Wojcicki, A. J. Am. Chem. Soc. 1973, 95, 6962-6970
8. Iron-carbon bond cleavage in strong carboxylic acids: De Luca, N.; Wojcicki, A. J. Organomet. Chem. 1980, 193, 359-378
9. 2 affording ArHgX: Dizikes, L. J.; Wojcicki, A. J. Am. Chem. Soc. 1977, 99, 5295-5303
10. Electrochemical behavior: Magdesieva, T. V.; Kukhareva, I. I.; Artamkina, G. A.; Beletskaya, I. P.; Butin, K. P. Izv. Akad. Nauk, SSSR Ser. Khim. 1996, 1812-1821
11. Photochemical behavior: Nesmeyanov, A. N.; Chapovskii, Y. A.; Polovyanyuk, I. V.; Makarova, L. G. Izv. Akad. Nauk, SSSR Ser. Khim. 1968, 1628-1629
12. Nesmeyanov, A. N.; Chapovskii, Y. A.; Lokshin, B. V.; Polovyanyuk, I. V.; Makarova, L. G. Dok. Akad. Nauk, SSSR 1966, 166, 1125-1128
13. Cp ring lithiation reaction: Orlova, T. Y.; Setkina, V. N.; Sizoi, V. F.; Kursanov, D. N. J. Organomet. Chem. 1983, 252, 201-204
14. Yasuda, S.; Yorimitsu, H.; Oshima, K. Organometallics 2008, 27, 4025-4027
15. Asada, Y.; Yasuda, S.; Yorimitsu, H.; Oshima, K. Organometallics 2008, 27, 6050-6052
16. Yasuda, S.; Asada, Y.; Yorimitsu, H.; Oshima, K. Materials 2009, 2, 978-991
17. Yasuda, S.; Yorimitsu, H.; Oshima, K. Organometallics 2009, 28, 4872-4875
18. Yasuda, S.; Yorimitsu, H.; Oshima, K. Organometallics 2010, 29, 273-274
19. 2Ar]: Butler, I. R.; Lindsell, W. E.; Preston, P. N. J. Chem. Res. Synop. 1981, 185
20. Artamkina, G. A.; Milchenko, A. Y.; Bumagin, N. A.; Beletskaya, I. P.; Reutov, O. A. Organomet. Chem., USSR 1988, 1, 17-20
21. Nesmeyanov, A. N.; Chapovsky, Y. A.; Polovyanyuk, I. V.; Makarova, L. G. J. Organomet. Chem. 1967, 7, 329-337
22. Hunter, A. D.; Szigety, A. B. Organometallics 1989, 8, 2670 - 2679, and references therein.
23. Recent examples of methods for the preparation of unsymmetrical stilbenes. Kormos, C. M.; Leadbeater, N. E. J. Org. Chem. 2008, 73, 3854-3858
24. Kabir, M. S.; Monte, A.; Cook, J. M. Tetrahedron Lett. 2007, 48, 7269-7273
25. 2H] with α-cyclopropylstyrene has been reported: Bullock, R. M.; Samsel, E. G. J. Am. Chem. Soc. 1990, 112, 6886-6898
26. 2(alkyl)]: Alt, H. G. Angew. Chem., Int. Ed. Engl. 1984, 23, 766-782
27. Waltz, K. M.; Muhoro, C. N.; Hartwig, J. F. Organometallics 1999, 18, 3383-3393
28. It was reported that similar gem -difluoroalkenes were obtained in rhodium-catalyzed addition reactions of arylboron reagents to α-trifluoromethylstyrene through β-fluoride elimination: Miura, T.; Ito, Y.; Murakami, M. Chem. Lett. 2008, 37, 1006-1007
29. Xi, Z.; Liu, B.; Chen, W. J. Org. Chem. 2008, 73, 3954-3957
30. Velder, J.; Ritter, S.; Lex, J.; Schmalz, H.-G. Synthesis 2006, 273-278
31. Itami, K.; Tonogaki, K.; Nokami, T.; Ohashi, Y.; Yoshida, J. Angew. Chem., Int. Ed. 2006, 45, 2404-2409
32. Cella, R.; Stefani, H. A. Tetrahedron 2006, 62, 5656-5662
33. Chen, Y.; Huang, L.; Ranade, M. A.; Zhang, X. P. J. Org. Chem. 2003, 68, 3714-3717
34. Lindh, J.; Enquist, P.-A.; Pilotti, Å.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957-7962
35. Katritzky, A. R.; Cheng, D.; Henderson, S. A.; Li, J. J. Org. Chem. 1998, 63, 6704-6709
36. Guo, H.; Ma, S. Synthesis 2007, 2731-2745
37. Zhang, T.-K.; Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Org. Lett. 2008, 10, 5337-5340
38. Cui, X.; Li, Z.; Tao, C.-Z.; Xu, Y.; Li, J.; Liu, L.; Guo, Q.-X. Org. Lett. 2006, 12, 2467-2470
39. Nakao, Y.; Imanaka, H.; Sahoo, A. K.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952-6953
40. Oehlke, A.; Auer, A. A.; Jahre, I.; Walfort, B.; Rüffer, T.; Zoufalá, P.; Lang, H.; Spange, S. J. Org. Chem. 2007, 72, 4328-4339