Palladium-catalyzed decarboxylative trifluoroethylation of aryl alkynyl carboxylic acids

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3267-3271

  Hwang, Jinil ^a   Park, Kyungho ^a   Choe, Juseok ^a   Min, Hongkeun ^a   Song, Kwang Ho ^b   Lee, Sunwoo ^a  

^a Chonnam National University   (South Korea)

^b Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FUNCTIONAL GROUPS; ORGANIC SOLVENTS;

ALKYNYLS; CATALYTIC SYSTEM; DECARBOXYLATIVE COUPLINGS; N ,N-DIMETHYLFORMAMIDE; PALLADIUM-CATALYZED;

CARBOXYLIC ACIDS;

ARYL ALKYNYL CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PALLADIUM; TOLUENE; UNCLASSIFIED DRUG; ALKYNE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID; CESIUM; CESIUM CARBONATE; FLUORINATED HYDROCARBON; N,N DIMETHYLFORMAMIDE;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; SONOGASHIRA REACTION; TRIFLUOROETHYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; CARBONATES; CARBOXYLIC ACIDS; CATALYSIS; CESIUM; DIMETHYLFORMAMIDE; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84898060263     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5003032     Document Type: Article

References (49)

1. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455-529
2. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
3. Bégué, J.-P.; Beonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992-1021
4. Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303-319
5. Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem., Int. Ed. 2009, 48, 4332-4336
6. Jin, Z.; Hammond, G. B.; Xu, B. Aldrichimica Acta 2012, 45, 67-83
7. Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401-10404
8. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795-10798
9. Tlili, A.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 6818-6819
10. Chan, K. S. L.; Wasa, M.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 9081-9084
11. Peng, H.; Liu, G. Org. Lett. 2011, 13, 772-775
12. Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713-3715
13. Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106-2109
14. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679-1681
15. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034-9037
16. McReynolds, K. A.; Lewis, R. S.; Akerman, L. K. G.; Dubinina, G. G.; Brennessel, W. W.; Vicic, D. A. J. Fluorine Chem. 2010, 131, 1108-1112
17. Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882-2885
18. Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769-10772
19. Luo, D.-F.; Xu, J.; Fu, Y.; Guo, Q.-X. Tetrahedron Lett. 2012, 53, 2769-2772
20. Zhang, L.-S.; Chen, K.; Chen, G.; Li, B.-J.; Luo, S.; Guo, Q.-Y.; Wei, J.-B.; Shi, Z.-J. Org. Lett. 2013, 15, 10-13
21. Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536-539
22. Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251-1257
23. Mazzotti, A. R.; Campbell, M. G.; Tang, P.; Murphy, J. M.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 14012-14015
24. Gao, Z.; Gouverneur, F.; Davis, B. G. J. Am. Chem. Soc. 2013, 135, 13612-13615
25. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342-9345
26. Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Yu, Y.-Q.; Zhang, F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781-9785
27. Arcadi, A.; Pietropaolo, E.; Alvino, A.; Michelet, V. Org. Lett. 2013, 15, 2766-2769
28. Bloom, S.; Pitts, C. R.; Woltornist, R.; Giswold, A.; Holl, M. G.; Lectka, T. Org. Lett. 2013, 15, 1722-1724
29. Li, Z.; Song, L.; Li, C. J. Am. Chem. Soc. 2013, 135, 4640-4643
30. Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198-2202
31. McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921-5940
32. Solladie-Cavallo, A.; Suffert, J. Tetrahedron Lett. 1984, 25, 1897-1900
33. Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398-3416
34. Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 1033-1036
35. Long, Z.-Y.; Chen, Q.-Y. Tetrahedron Lett. 1998, 39, 8487-8490
36. Matsuya, Y.; Ihara, D.; Fukuchi, M.; Honma, D.; Itoh, K.; Tabuchi, A.; Nemoto, H.; Tsuda, M. Bioorg. Med. Chem. 2012, 20, 2564-2571
37. Feng, Y.-S.; Xie, C.-Q.; Qiao, W.-L.; Xu, H.-J. Org. Lett. 2013, 15, 936-939
38. Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596-3599
39. Liu, C.-B.; Meng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J.-A. Angew. Chem., Int. Ed. 2012, 51, 6227-6230
40. Zhao, T. S. N.; Szabó, K. J. Org. Lett. 2012, 14, 3966-3969
41. Park, K.; You, J.-M.; Jeon, S.; Lee, S. Eur. J. Org. Chem. 2013, 1973-1978
42. Park, K.; Palani, T.; Pyo, A.; Lee, S. Tetrahedron Lett. 2012, 53, 733-737
43. Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945-948
44. Park, K.; Lee, S. RSC Adv. 2013, 3, 14165-14182
45. Goossen, L. J.; Goosen, K. Top. Organomet. Chem. 2013, 44, 121-142
46. Shang, R.; Liu, L. Sci. China: Chem. 2011, 54, 1670-1687
47. Dzik, W. I.; Lange, P. P.; Gooßen, L. J. Chem. Sci. 2012, 3, 2671-2678
48. Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030-5048
49. Miyake, Y.; Ota, S.-i.; Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7809-7811