An I2O5-promoted decarboxylative trifluoromethylation of cinnamic acids

Tetrahedron Letters

Volumn 56, Issue 1, 2015, Pages 233-235

  Shang, Xiao Jie ^a   Li, Zejiang ^b   Liu, Zhong Quan ^b  

^a GANSU AGRICULTURAL UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Cinnamic acid; Decarboxylation; Free radical; Sodium trifluoromethanesulfinate; Trifluoromethylation

Indexed keywords

ALKENE; CINNAMIC ACID; INORGANIC COMPOUND; IODINE PENTOXIDE; SODIUM TRIFLUOROMETHANESULFINATE; SULFINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECARBOXYLATION; METHYLATION;

EID: 84919488705     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.11.076     Document Type: Article

References (62)

1. For selected reviews on trifluoromethylation, see: T. Umemoto Chem. Rev. 96 1996 1757
2. G.K.S. Prakash, and A.K. Yudin Chem. Rev. 97 1997 757
3. R.P. Singh, and J.M. Shreeve Tetrahedron 56 2000 7613
4. J.-A. Ma, and D. Cahard Chem. Rev. 104 2004 6119
5. M. Shimizu, and T. Hiyama Angew. Chem., Int. Ed. 44 2005 214
6. M. Schlosser Angew. Chem., Int. Ed. 45 2006 5432
7. K. Müller, C. Faeh, and F. Diederich Science 1881 2007 317
8. G.K.S. Prakash, and J. Hu Acc. Chem. Res. 40 2007 921
9. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
10. J. Hu, W. Zhang, and F. Wang Chem. Commun. 2009 7465
11. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470
12. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475
13. X.-F. Wu, H. Neumann, and M. Beller Chem. Asian J. 7 2012 1744
14. Z. Jin, G.B. Hammond, and B. Xu Aldrichim. Acta 45 2012 67
15. Y. Ye, and M.S. Sanford Synlett 2005 23
16. T. Besset, C. Schneider, and D. Cahard Angew. Chem., Int. Ed. 51 2012 5048
17. Y. Macé, and E. Magnier Eur. J. Org. Chem. 2012 2479
18. T. Liang, C.N. Neumann, and T. Ritter Angew. Chem., Int. Ed. 52 2013 8214
19. H. Liu, Z. Gu, and X. Jiang Adv. Synth. Catal. 355 2013 617
20. For reviews on free-radical trifluoromethylation, see: A. Studer Angew. Chem., Int. Ed. 51 2012 8950
21. X. Wang, Y. Zhang, and J. Wang Sci. China Chem. 42 2012 1
22. S. Barata-Callejo, and A. Postigo Coord. Chem. Rev. 257 2013 3051
23. For selected recent examples of free-radical trifluoromethylation, see: D.A. Nagib, and D.W.C. MacMillan Nature 480 2011 224
24. J.D. Nguyen, J.W. Tucker, M.D. Konieczynska, and C.R.J. Stephenson J. Am. Chem. Soc. 133 2011 4160
25. P.V. Pham, D.A. Nagib, and D.W.C. MacMillan Angew. Chem., Int. Ed. 50 2011 6119
26. Y. Ye, and M.S. Sanford J. Am. Chem. Soc. 134 2012 9034
27. C.J. Wallentin, J.D. Nguyen, P. Finkbeiner, and C.R.J. Stephenson J. Am. Chem. Soc. 134 2012 8875
28. Y. Yasu, T. Koike, and M. Akita Angew. Chem., Int. Ed. 51 2012 9567
29. R. Zhu, and S.L. Buchwald J. Am. Chem. Soc. 134 2012 12462
30. Y. Li, and A. Studer Angew. Chem., Int. Ed. 51 2012 8221
31. Y.-T. He, L.-H. Li, Y.-F. Yang, Y.-Q. Wang, J.-Y. Luo, X.-Y. Liu, and Y.-M. Liang Chem. Commun. 2013 5687
32. D.-F. Lu, C.-L. Zhu, and H. Xu Chem. Sci. 4 2013 2478
33. R. Zhu, and S.L. Buchwald Angew. Chem., Int. Ed. 52 2013 12655
34. W. Kong, M. Casimiro, E. Merino, and C. Nevado J. Am. Chem. Soc. 135 2013 14480
35. W. Kong, M. Casimiro, E. Merino, and C. Nevado Angew. Chem., Int. Ed. 52 2013 13086
36. H. Egami, R. Shimizu, S. Kawamura, and M. Sodeoka Angew. Chem., Int. Ed. 52 2013 4000
37. D.J. Wilger, N.J. Gesmundo, and D.A. Nicewicz Chem. Sci. 4 2013 3160
38. N. Iqbal, J. Jung, S. Park, and E.J. Cho Angew. Chem., Int. Ed. 52 2013 539
39. X. Liu, F. Xiong, X. Huang, L. Xu, P. Li, and X. Wu Angew. Chem., Int. Ed. 52 2013 6962
40. Z.-M. Chen, W. Bai, S.-H. Wang, B.-M. Yang, Y.-Q. Tu, and F.-M. Zhang Angew. Chem., Int. Ed. 52 2013 9781
41. F. Wang, X. Qi, Z. Liang, P. Chen, and G. Liu Angew. Chem., Int. Ed. 2014 1881 53
42. T. Xu, C.-W. Cheung, and X. Hu Angew. Chem., Int. Ed. 53 2014 4910
43. For selected examples of trifluoromethylation by using Langlois reagent, see: B.R. Langlois, E. Laurent, and N. Roidot Tetrahedron Lett. 32 1991 7525
44. Y. Fujiwara, J.A. Dixon, F. O'Hara, E.D. Funder, D.D. Dixon, R.A. Rodriguez, R.D. Baxter, B. Herlé, N. Sach, M.R. Collins, Y. Ishihara, and P.S. Baran Nature 492 2012 95
45. F. O'Hara, D.G. Blackmond, and P.S. Baran J. Am. Chem. Soc. 135 2013 12122
46. Y. Li, L. Wu, H. Neumann, and M. Beller Chem. Commun. 2013 2628
47. Y. Ji, T. Brueckl, R.D. Baxter, Y. Fujiwara, I.B. Seiple, S. Su, D.G. Blackmond, and P.S. Baran Proc. Natl. Acad. Sci. U.S.A. 108 2011 14411
48. Y. Ye, S.A. Künzi, and M.S. Sanford Org. Lett. 14 2012 4979
49. A. Deb, S. Manna, A. Modak, T. Patra, S. Maity, and D. Maiti Angew. Chem., Int. Ed. 52 2013 9747
50. X.-Y. Jiang, and F.-L. Qing Angew. Chem., Int. Ed. 52 2013 14177
51. Z. Li, Z. Cui, and Z.-Q. Liu Org. Lett. 15 2013 406
52. L. Zhang, Z. Li, and Z.-Q. Liu Org. Lett. 16 2014 3688
53. Z. Hang, Z. Li, and Z.-Q. Liu Org. Lett. 16 2014 3648
54. Z. Cui, X. Shang, X.-F. Shao, and Z.-Q. Liu Chem. Sci. 3 2012 2853
55. Z. He, T. Luo, M. Hu, Y. Cao, and J. Hu Angew. Chem., Int. Ed. 51 2012 3944
56. T. Patra, A. Deb, S. Manna, U. Sharma, and D. Maiti Eur. J. Org. Chem. 2013 5247
57. A.T. Parsons, T.D. Senecal, and S.L. Buchwald Angew. Chem., Int. Ed. 51 2012 2947
58. J. Xu, D.-F. Luo, B. Xiao, Z.-J. Liu, T.-J. Gong, Y. Fu, and L. Liu Chem. Commun. 2011 4300
59. T. Liu, and Q. Shen Org. Lett. 13 2011 2342
60. E.J. Cho, and S.L. Buchwald Org. Lett. 13 2011 6552
61. J. Yin, Y. Li, R. Zhang, K. Jin, and C. Duan Synthesis 46 2014 607
62. C.-X. Zhao, Y.-Y. Peng, Y.-L. Qu, and H. Peng Chem. J. Chin. Univ. 13 1992 1448