Highly regioselective Heck-Mizoroki reaction catalyzed by Pd/phosphine ligand in DMSO/[bmim][BF4] under microwave irradiation

Arkivoc

Volumn 2012, Issue 6, 2012, Pages 164-172

  Zhou, Zhonggao ^a,b   Xie, Yongrong ^a   Du, Ziyi ^a   Hu, Qiaosheng ^a   Xue, Jun ^a   Shi, Jicheng ^b  

^a GANNAN NORMAL UNIVERSITY   (China)

^b FUJIAN NORMAL UNIVERSITY   (China)

Author keywords

Heck reaction; Ionic liquid; Microwave heating; Palladium catalyst; Regioselectivity

Indexed keywords

EID: 84863377236     PISSN: 15517012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0013.615     Document Type: Article

References (46)

1. (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
2. (b) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
3. (c) Negishi, E.; De Meijere, A., Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley: New York, 2002.
4. (d) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
5. (e) Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007, 5, 31.
6. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
7. (a) Trejos, A.; Fardost, A.; Yahiaoui, S.; Larhed, M. Chem. Commun. 2009, 7587
8. (b) Yahiaoui, S.; Fardost, A.; Trejos, A.; Larhed, M. J. Org. Chem. 2011, 76, 2433.
9. (c) Liao, L. Y.; Jana, R. J.; Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 5784.
10. (d) Wang, L.; Li, H.; Li, P. Tetrahedron 2009, 65, 364.
11. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
12. (b) Dounay, A. B.; Overman, L. E. The Asymmetric Intramolecular Mizoroki-Heck Reaction in Natural Product Total Synthesis, Wiley: New York, 2009, p 533.
13. (c) Moro, A. L. V.; Cardoso, F. V. S. P.; Correia, C. R. D. Org. Lett. 2009, 11, 3642.
14. (a) Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751.
15. (b) Ruan, J. W.; Xiao, J. L. Acc. Chem. Res. 2011, 44, 614.
16. Olofsson, K.; Larhed, M.; Hallberg, A. J. Org. Chem. 1998, 63, 5076.
17. (a) Andreu, M. G.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475.
18. (b) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120.
19. (c) Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2005, 70, 1786.
20. (d) Demir, S.; Özdemir, I.; Çetinkaya, B. Appl. Organomet. Chem. 2006, 20, 254
21. (e) Dawood, K. Tetrahedron 2007, 63, 9642.
22. (f) Shaaban, M. R.; Darweesh, A. F.; Dawood, K. M.; Farag, A. M. Arkivoc 2010, (x), 208.
23. (g) Huang, S. H.; Chen, J. R.; Tsai, F. Y. Molecules 2010, 15, 315.
24. (h) Küçükbay, H.; Şireci, N.; Yilmaz, Ü.; Akkurt, M.; Yalçin, Ş. P.; Nawaz Tahir, M.; Ott, H. Appl. Organomet. Chem. 2011, 25, 255.
25. (i) Allam, B. K.; Singh, K. N. Synthesis 2011, 2011, 1125
26. (j) Du, Z.; Zhou, W.; Bai, L.; Wang, F.; Wang, J. X. Synlett 2011, 2011, 369.
27. (k) Majumdar, K. C.; Ray, K.; Ganai, S. Tetrahedron Lett. 2010, 51, 1736.
28. Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2005, 70, 1786.
29. Hajipour, A. R.; Rafiee, F. Appl. Organomet. Chem. 2011, 25, 542.
30. (a) Xu, L.; Chen, W.; Ross, J.; Xiao, J. Org. Lett. 2001, 3, 295.
31. (b) Mo, J.; Liu, S.; Xiao, J. Tetrahedron 2005, 61, 9902.
32. (a) Mo, J.; Xiao, J. Angew. Chem. Int. Ed. 2006, 45, 4152.
33. (b) Ruan, J. W.; Iggo, J. A.; Berry, N. G.; Xiao, J. L. J. Am. Chem. Soc. 2010, 132, 16689.
34. (a) Shi, J. C.; Hong, M. C.; Wu, D. X.; Liu, Q. T.; Kang, B. S. Chem. Lett. 1995, 685.
35. (b) Shi, J. C.; Wen, T. B.; Wu, D. X.; Lu, G. T.; Hong, M. C.; Liu, Q. T.; Kang, B. S.; Wang, H. Q.; Lu, S. J. Chin. J. Chem. 1996, 14, 454.
36. Zheng, J.; Zhou, Z. G.; Tong, Q. S.; Jiang, F.; Jia, L.; Lin, J. H.; Shi, J. C. Chin. J. Org. Chem. 2011, 31, 324.
37. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
38. Hallett, J. P.; Welton, T. Chem. Rev. 2011, 111, 3508.
39. Luche, J. L.; Einhorn, C.; Einhorn, J. V.; Sinisterra-Gago, J. V. Tetrahedron Lett. 1990, 31,4125.
40. Klingshirn, M. A.; Broker, G. A.; Holbrey, J. D.; Shaughnessy, K. H.; Rogers, R. D. Chem. Commun. 2002, 1394.
41. (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387.
42. (b) Herrmann, W. A.; Brossmer, C.; Oefele, K.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem. 1995, 103, 133.
43. (c) Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119.
44. Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241.
45. Iranpoor, N.; Firouzabadi, H.; Azadi, R. Eur. J. Org. Chem. 2007, 2007, 2197.
46. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books: Mill Valley, CA, 1994.