Palladium(II)-catalyzed directed trifluoromethylthiolation of unactivated C(sp3)-H bonds

Journal of Organic Chemistry

Volumn 80, Issue 8, 2015, Pages 4204-4212

  Xiong, Heng Ying ^a   Besset, Tatiana ^a   Cahard, Dominique ^a   Pannecoucke, Xavier ^a  

^a NORMANDIE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AMIDES; CATALYSIS;

ALIPHATIC ACIDS; BOND FORMATION; C-H ACTIVATION; DIRECTING GROUPS; FUNCTIONALIZATIONS; H-BONDS; PIVALIC ACID;

PALLADIUM COMPOUNDS;

AMIDE; CARBON; CARBOXYLIC ACID DERIVATIVE; HYDROCINNAMIC ACID DERIVATIVE; HYDROGEN; PALLADIUM; PHENYLACETIC ACID DERIVATIVE; PHTHALIMIDE DERIVATIVE; PIVALIC ACID;

ARTICLE; CATALYST; CHELATION; CONTROLLED STUDY; COVALENT BOND; ELECTRON; ELECTROPHILICITY; HYDROGEN BOND; OXIDATION; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 84928473165     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00505     Document Type: Article

References (80)

1. For a special issue on fluorine chemistry, see: Chem. Rev. 2015, 115, 563-1306.
2. Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476
3. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
4. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
5. Besset, T.; Poisson, T.; Pannecoucke, X. Chem.-Eur. J. 2014, 20, 16830
6. Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941
7. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048
8. Catalán, S.; Munoz, S. B.; Fustero, S. Chimia 2014, 68, 382
9. Cahard, D.; Bizet, V. Chem. Soc. Rev. 2014, 43, 135
10. OHagan, D. Chem. Soc. Rev. 2008, 37, 308
11. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
12. Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem. 2004, 5, 637
13. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
14. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832
15. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
16. Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207
17. Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2415 and references therein
18. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731 and references therein
19. Alazet, S.; Zimmer, L.; Billard, T. Chem.-Eur. J. 2014, 20, 8589
20. Huang, Y.; He, X.; Lin, X.; Rong, M.; Weng, Z. Org. Lett. 2014, 16, 3284
21. Hu, M.; Rong, J.; Miao, W.; Ni, C.; Han, Y.; Hu, J. Org. Lett. 2014, 16, 2030
22. Zhu, L.; Wang, G.; Guo, Q.; Xu, Z.; Zhang, D.; Wang, R. Org. Lett. 2014, 16, 5390
23. Liu, J.-B.; Xu, X.-H.; Chen, Z.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 897
24. Yang, T.; Lu, L.; Shen, Q. Chem. Commun. 2015, 51, 5479
25. Dai, X.; Cahard, D. Synlett 2015, 26, 40
26. Ye, K.-Y.; Zhang, X.; Dai, L.-X.; You, S.-L. J. Org. Chem. 2014, 79, 12106
27. Huang, Z.; Yang, Y.-D.; Tokunaga, E.; Shibata, N. Org. Lett. 2015, 17, 1063
28. Danoun, G.; Bayarmagnai, B.; Gruenberg, M. F.; Goossen, L. J. Chem. Sci. 2014, 5, 1312
29. Zhang, K.; Liu, J.-B.; Qing, F.-L. Chem. Commun. 2014, 50, 14157
30. Shi, G.; Zhang, Y. Adv. Synth. Catal. 2014, 356, 1419
31. Miura, M.; Satoh, T.; Hirano, K. Bull. Chem. Soc. Jpn. 2014, 87, 751
32. De Sarkar, S.; Liu, W.; Kozhushkov, S. I.; Ackermann, L. Adv. Synth. Catal. 2014, 356, 1461
33. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
34. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
35. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362
36. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
37. Arockiam, P. B.; Bruneau, C.; Dixneuf Chem. Rev. 2012, 112, 5879
38. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
39. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
40. Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74
41. Zhang, Q.; Chen, K.; Shi, B.-F. Synlett 2014, 25, 1941
42. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
43. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464
44. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
45. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
46. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191
47. Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Chem. Soc. Rev. 2014, 44, 291
48. Yan, S.-Y.; Liu, Y.-J.; Liu, B.; Liu, Y.-H.; Shi, B.-F. Chem. Commun. 2015, 51, 4069
49. Yang, K.; Wang, Y.; Chen, X.; Kadi, A. A.; Fun, H.-K.; Sun, H.; Zhang, Y.; Lu, H. Chem. Commun. 2015, 51, 3582
50. Chu, L.; Yue, X.; Qing, F.-L. Org. Lett. 2010, 12, 1644
51. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
52. Iwasaki, M.; Iyanaga, M.; Tsuchiya, Y.; Nishimura, Y.; Li, W.; Li, Z.; Nishihara, Y. Chem.-Eur. J. 2014, 20, 2459
53. Yang, Y.; Hou, W.; Qin, L.; Du, J.; Feng, H.; Zhou, B.; Li, Y. Chem.-Eur. J. 2014, 20, 416
54. Li, X.; Xu, Y.; Wu, W.; Jiang, C.; Qi, C.; Jiang, H. Chem.-Eur. J. 2014, 20, 7911
55. Chen, F.-J.; Liao, G.; Li, X.; Wu, J.; Shi, B.-F. Org. Lett. 2014, 16, 5644
56. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
57. Xu, C.; Shen, Q. Org. Lett. 2014, 16, 2046
58. Yin, W.; Wang, Z.; Huang, Y. Adv. Synth. Catal. 2014, 356, 2998
59. 3)-H bonds of aliphatic amides was reported: Lin, C.; Yu, W.; Yao, J.; Wang, B.; Liu, Z.; Zhang, Y. Org. Lett. 2015, 17, 1340
60. Chen, C.; Xu, X.-H.; Yang, B.; Qing, F.-L. Org. Lett. 2014, 16, 3372
61. Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457
62. Guo, S.; Zhang, X.; Tang, P. Angew. Chem., Int. Ed. 2015, 54, 4065
63. Wu, H.; Xiao, Z.; Wu, J.; Guo, Y.; Xiao, J.-C.; Liu, C.; Chen, Q.-Y. Angew. Chem., Int. Ed. 2015, 54, 4070
64. Besset, T.; Cahard, D.; Pannecoucke, X. J. Org. Chem. 2014, 79, 413
65. Belhomme, M.-C.; Dru, D.; Xiong, H.-Y.; Cahard, D.; Besset, T.; Poisson, T.; Pannecoucke, X. Synthesis 2014, 1859
66. Belhomme, M.-C.; Poisson, T.; Pannecoucke, X. Org. Lett. 2013, 15, 3428
67. Besset, T.; Poisson, T.; Pannecoucke, X. Eur. J. Org. Chem. 2014, 7220
68. Racowski, J. M.; Ball, N. D.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18022
69. McMurtrey, K. B.; Racowski, J. M.; Sanford, M. S. Org. Lett. 2012, 14, 4094
70. Rit, R. K.; Yadav, M. R.; Sahoo, A. K. Org. Lett. 2012, 14, 3724
71. Rit, R. K.; Yadav, M. R.; Ghosh, K.; Shankar, M.; Sahoo, A. K. Org. Lett. 2014, 16, 5258
72. Wang, Z.; Kuninobu, Y.; Kanai, M. Org. Lett. 2014, 16, 4790
73. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342
74. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030
75. Wang, Z.; Ni, J.; Kuninobu, Y.; Kanai, M. Angew. Chem., Int. Ed. 2014, 53, 3496
76. Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457
77. Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316
78. Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2009, 131, 7558
79. Besset, T.; Kuhl, N.; Patureau, F. W.; Glorius, F. Chem.-Eur. J. 2011, 17, 7167
80. Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650