Difunctionalization of alkenes via the visible-light-induced trifluoromethylarylation/1,4-Aryl shift/desulfonylation cascade reactions

Journal of Organic Chemistry

Volumn 80, Issue 11, 2015, Pages 5730-5736

  Zheng, Lewei ^a   Yang, Chao ^a   Xu, Zhaozhong ^a   Gao, Fei ^a   Xia, Wujiong ^a  

^a HARBIN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

CASCADE REACTIONS; DIFUNCTIONALIZATION; OXINDOLES; TRIFLUOROMETHYL; VISIBLE LIGHT INDUCED;

LIGHT;

ALKENE DERIVATIVE; ISOQUINOLINE DERIVATIVE; OXINDOLE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ALKENE; FLUORINATED HYDROCARBON; INDOLE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; ARYLATION; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT;

ALKENES; CATALYSIS; HYDROCARBONS, FLUORINATED; INDOLES; ISOQUINOLINES; LIGHT; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS;

EID: 84930960132     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00677     Document Type: Article

References (56)

1. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787
2. Weinreb, S. M. Chem. Rev. 2006, 106, 2531
3. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, U.K., 2009.
4. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis Reactivity Applications; Wiley-VCH: Weinheim, Germany, 2004.
5. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
6. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455
7. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048
8. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
9. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462
10. Zhang, X.-G.; Dai, H.-X.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948
11. Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257
12. Zhang, L.; Chen, K.; Chen, G.; Li, B.; Luo, S.; Guo, Q.; Wei, J.; Shi, Z. Org. Lett. 2013, 15, 10
13. Egami, H.; Shimizu, R.; Kawamura, S.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 4000
14. Kong, W.; Casimiro, M.; Fuentes, N.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 13086
15. Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480
16. Li, L.; Deng, M.; Zhang, S.-C.; Xiong, Y.-P.; Tan, B.; Liu, X.-Y. Org. Lett. 2014, 16, 504
17. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527
18. Maity, S.; Zheng, N. Synlett 2012, 1851
19. Yoon, T. P. ACS. Catal. 2013, 3, 895
20. Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859
21. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828
22. Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785
23. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617
24. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102
25. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
26. Shi, L.; Xia, W.-J. Chem. Soc. Rev. 2012, 41, 7687
27. Xi, H. Y. Y.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387
28. Xu, P.; Xie, J.; Xue, Q.-C.; Pan, C.-D.; Cheng, Y.-X.; Zhu, C.-J. Chem.-Eur. J. 2013, 19, 14039
29. Wilger, D. J.; Gesmundoa, N. J.; Nicewicz, D. A. Chem. Sci. 2013, 4, 3160
30. Wallentin, C.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875
31. Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136
32. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160
33. Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2013, 49, 2037
34. Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; Duill, M. O.; Wheelhouse, K.; Rassias, G.; Mdebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505
35. Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem.-Eur. J. 2013, 19, 6209
36. Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383
37. Mizuta, S.; Engle, K. M.; Verhoog, S.; GaliciaLopez, O.; ODuill, M.; Medebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250
38. Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567
39. Oh, S. H.; Malpani, Y. R.; Ha, N.; Jung, Y. S.; Han, S. B. Org. Lett. 2014, 16, 1310
40. Zhao, G.-L.; Yang, C.; Guo, L.; Sun, H.-N.; Lin, R.; Xia, W.-J. J. Org. Chem. 2012, 77, 6302
41. Zhao, Y.-T.; Li, Z.; Yang, C.; Lin, R.; Xia, W.-J. Beilstein J. Org. Chem. 2014, 10, 622
42. Sun, H.-N.; Yang, C.; Lin, R.; Xia, W.-J. Adv. Synth. Catal. 2014, 356, 2775
43. Sun, H.-N.; Yang, C.; Gao, F.; Li, Z.; Xia, W.-J. Org. Lett. 2013, 15, 624
44. Zhao, G. L.; Yang, C.; Guo, L.; Sun, H.-N.; Chen, C.; Xia, W.-J. Chem. Commun. 2012, 48, 2337
45. Guo, L.; Yang, C.; Zheng, L.-W.; Xia, W.-J. Org. Biomol. Chem. 2013, 11, 5787
46. Li, X.-Q.; Xu, X.-S.; Hu, P.-Z.; Xiao, X.-Q.; Zhou, C. J. Org. Chem. 2013, 78, 7343
47. Anna, U.; Maciej, S.; Stefanie V, K.; Christoph, P.; Alexander, P.; Wolfgang, B.; Tanja, G. Chem.-Eur. J. 2015, 21, 1444
48. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
49. Koike, T.; Akita, M. Top. Catal. 2014, 57, 967
50. Jiang, H.; Huang, C.-M.; Guo, J.-J.; Zeng, C.-Q.; Zhang, Y.; Yu, S.-Y. Chem.-Eur. J. 2012, 18, 15158
51. Kamiqata, N.; Fukushima, T.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1989, 1559
52. Xu, J.; Liu, X.-Y.; Fu, Y. Tetrahedron Lett. 2014, 55, 585
53. Koike, T.; Akita, M. J. Fluorine Chem. 2014, 167, 30
54. Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598
55. Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294
56. Rey, V.; Pierini, A. B.; Penenory, A. B. J. Org. Chem. 2009, 74, 1223