Synthesis of fluorovinyl aryl ethers by a three-component reaction of gem-difluoroalkenes with arylboronic acids and oxygen

RSC Advances

Volumn 5, Issue 16, 2015, Pages 11996-11999

  Wang, Mingjin ^a   Liang, Fang ^a   Xiong, Yang ^a   Cao, Song ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; OXYGEN;

ARYL ETHER; ARYLBORONIC ACIDS; METAL-FREE CONDITIONS; THREE COMPONENT REACTIONS;

SYNTHESIS (CHEMICAL);

EID: 84922156865     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra16468g     Document Type: Article

References (44)

1. (a) D. K. Dei, B. R. Lund, J.-B. Wu, D. Simon, T. Ware, W. E. Voit, D. MacFarlane, S. M. Liff and D. W. Smith Jr, ACS Macro Lett., 2013, 2, 35;
2. (b) S. Keck, T. A. Knoerzer, D. W. Smith Jr and S. T. Lacono, Polym. Int., 2013, 62, 1485;
3. (c) S.-B. Lee, Y.-J. Kim, U. Ko, C.-M. Min, M.-K. Ahn, S.-J. Chung, I.-S. Moon and J.-S. Lee, J. Membr. Sci., 2014, 456, 49;
4. (d) C. Yuan, K.-K. Jin, K. Li, S. Diao, J.-W. Tong and Q. Fang, Adv. Mater., 2013, 25, 4875;
5. (e) E. L. Luzina and A. V. Popov, Eur. J. Med. Chem., 2009, 44, 4944;
6. (f) J.-K. Kim, D.-H. Kim, H.-H. Kim, K.-H. Kim, C.-S. Yoon and I.-C. Hwang, WO Pat., 2009005297, 2009.
7. (a) A. V. Matsnev, S.-Y. Qing, M. A. Stanton, K. A. Berger, G. Haufe and J. S. Thrasher, Org. Lett., 2014, 16, 2402;
8. (b) G.-L. Lu, S. Zhang, Y.-J. Li and X.-Y. Huang, Chin. J. Chem., 2011, 29, 2791;
9. (c) T. Kita, K. Yokoyama, S. Ihara, T. Asai and H. Koh, WO Pat., 2013031603, 2013;
10. (d) P. G. Wilson, J. M. Percy, J. M. Redmond and A. W. McCarter, J. Org. Chem., 2012, 77, 6384.
11. (a) D. Kundu, P. Maity and B. C. Ranu, Org. Lett., 2014, 16, 1040;
12. (b) G. Nordmann and S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 4978;
13. (c) J. Limberger, B. C. Leal, D. F. Back, J. Dupont and A. L. Monteiro, Adv. Synth. Catal., 2012, 354, 1429;
14. (d) Z.-H. Wan, C. D. Jones, T. M. Koenig, Y. J. Pu and D. Mitchell, Tetrahedron Lett., 2003, 44, 8257.
15. E. Nomada, H. Watanabe, M. Yamamoto, T. Udagawa, B. Zhou, A. Kobayashi, M. Minakawa and M. Kawatsura, Synlett, 2014, 25, 1725.
16. (a) M. S. Kim and I. H. Jeong, Tetrahedron Lett., 2005, 46, 3545;
17. (b) X.-H. Huang, P.-Y. He and G.-Q. Shi, J. Org. Chem., 2000, 65, 627;
18. (c) T. Fujita, K. Sakoda, M. Ikeda, M. Hattori and J. Ichikawa, Synlett, 2013, 24, 57;
19. (d) J. Ichikawa, Y. Wada, M. Fujiwara and K. Sakoda, Synthesis, 2002, 13, 1917;
20. (e) K. Fuchibe, M. Takahashi and J. Ichikawa, Angew. Chem., Int. Ed., 2012, 51, 12059;
21. (f) J. A. Cooper, C. M. Olivares and G. Sandford, J. Org. Chem., 2001, 66, 4887;
22. (g) F. Tellier, M. Audouin and R. Sauvêtre, J. Fluorine Chem., 2002, 113, 167.
23. (a) J. D. Moody, D. VanDerveer, D. W. Smith Jr and S. T. Iacono, Org. Biomol. Chem., 2011, 9, 4842;
24. (b) H.-K. Wu, J.-Q. Zhong, H.-M. Shen and H.-X. Shi, J. Fluorine Chem., 2013, 156, 5;
25. (c) A. E. Feiring, S. Rozen and E. R. Wonchoba, J. Fluorine Chem., 1998, 89, 31;
26. (d) B. T. Kim, Y. K. Min, N. K. Park, K. Y. Cho and I. H. Jeong, Heterocycles, 1995, 41, 641.
27. (a) A. E. Feiring and E. R. Wonchoba, J. Org. Chem., 1992, 57, 7014;
28. (b) A. Fuss and V. Koch, Synthesis, 1990, 7, 604;
29. (c) M. M. Kremlev, A. I. Mushta and L. I. Moklyarchuk, Russ. J. Org. Chem., 2003, 39, 1125;
30. (d) E. Yang, M. R. Reese and J. M. Humphrey, Org. Lett., 2012, 14, 3944;
31. (e) J. Ichikawa, M. Kobayashi, N. Yokota, Y. Noda and T. Minami, Tetrahedron, 1994, 50, 11637;
32. (f) R. Arnold-Stanton and D. M. Lemal, J. Org. Chem., 1991, 56, 151.
33. (a) Y. Xiong, X.-X. Zhang, T. Huang and S. Cao, J. Org. Chem., 2014, 79, 6395;
34. (b) W.-P. Dai, J. Xiao, G.-Y. Jin, J.-J. Wu and S. Cao, J. Org. Chem., 2014, 79, 10537;
35. (c) G.-Y. Jin, J. Zhang, W. Wu and S. Cao, J. Fluorine Chem., 2014, 168, 240;
36. (d) X.-X. Zhang, Y.-Y. Lin, J. Zhang and S. Cao, RSC Adv., 2015, 5, 7905.
37. (a) D.-S. Chen and J.-M. Huang, Synlett, 2013, 24, 499;
38. (b) S.-M. Guo, L. Lu and H. Cai, Synlett, 2014, 24, 1712;
39. (c) Y.-Q. Zou, J.-R. Chen, X.-P. Liu, L.-Q. Lu, R. L. Davis, K. A. Jørgensen and W.-J. Xiao, Angew. Chem., Int. Ed., 2012, 51, 784;
40. (d) C. Zhu, R. Wang and J. R. Falck, Org. Lett., 2012, 14, 3494.
41. (a)M. Moreno-Mañas, M. Pérez and R. Pleixats, J. Org. Chem., 1996, 61, 2346;
42. (b) J.-Q. Liu and M. J. Robins, Org. Lett., 2004, 6, 3421;
43. (c) M. A. Aramendía and F. Lafont, J. Org. Chem., 1999, 64, 3592.
44. J. Zhang, J.-J. Wu, Y. Xiong and S. Cao, Chem. Commun., 2012, 48, 8553.