Catalytic trifluoromethylation of aryl- and vinylboronic acids by 2-cyclopropyl-1-(trifluoromethyl)benzo[ b ]thiophenium triflate

Organic Letters

Volumn 17, Issue 7, 2015, Pages 1632-1635

  Arimori, Sadayuki ^a   Shibata, Norio ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2-CYCLOPROPYL-1-(TRIFLUOROMETHYL)BENZO(B)THIOPHENIUM TRIFLATE; ACETIC ACID DERIVATIVE; ACETIC ACID ETHYL ESTER; BORONIC ACID DERIVATIVE; COPPER; FLUORINATED HYDROCARBON; GAMMA-COLLIDINE; MESYLIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; THIOPHENE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION;

ACETATES; BORONIC ACIDS; CATALYSIS; COPPER; HYDROCARBONS, FLUORINATED; MESYLATES; METHYLATION; MOLECULAR STRUCTURE; PYRIDINES; THIOPHENES; VINYL COMPOUNDS;

EID: 84926433752     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00164     Document Type: Article

References (40)

1. Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
4. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
5. Jeschke, P. ChemBioChem 2004, 5, 570
6. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C. d.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
7. Iseki, K.; Nagai, T.; Kobayashi, Y. Tetrahedron Lett. 1994, 35, 3137
8. Zhao, H.; Qin, B.; Liu, X.; Feng, X. Tetrahedron 2007, 63, 6822
9. Nagao, H.; Yamane, Y.; Mukaiyama, T. Chem. Lett. 2007, 36, 666
10. Mizuta, S.; Shibata, N.; Akiti, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Org. Lett. 2007, 9, 3707
11. Pouterman, E.; Girardet, A. Helv. Chim. Acta 1947, 30, 107
12. Alexandere, P.; Stephane, C.; Sylvette, B. J. Fluorine Chem. 2010, 131, 1241
13. Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 47, 4095
14. Kondratenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis 1980, 932
15. Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832
16. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
17. Morimoto, H.; Tsubogo, T.; Livitinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 123, 3877
18. Tomashenko, O. A.; Escudero-Adán, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 123, 7797
19. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Waston, D. A.; Buchwald, S. L. Science 2010, 328, 1679
20. Yagupol'skii, L. M.; Kondratenko, N. V.; Timolfeeva, G. N. J. Org. Chem. USSR 1984, 20, 103
21. Umemoto, T.; Ishihara, S. Tetrahedron Lett. 1990, 31, 3579
22. Yang, J.-J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1998, 63, 2656
23. Eisenberger, P.; Gischig, S.; Togni, A. Chem, Eur. J. 2006, 12, 2579
24. Noritake, S.; Shibata, N.; Nakamura, S.; Toru, T.; Shiro, M. Eur. J. Org. Chem. 2008, 3465
25. Matsnev, A.; Noritake, S.; Nomura, Y.; Tokunaga, E.; Nakamura, S.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 572
26. Zhang, C. Org. Biomol. Chem. 2014, 12, 6580
27. Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650
28. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986
29. Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342
30. Weng, Z.; Li, H.; He, W.; Yao, L.-F.; Tan, J.; Chen, J.; Yuan, Y.; Huang, K.-W. Tetrahedron 2012, 68, 2527
31. Deng, Q.-H.; Wadepohl, H.; Gade, L.-H. J. Am. Chem. Soc. 2012, 134, 10769
32. Egami, H.; Shimizu, S.; Kawamura, S.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 4000
33. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
34. Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300
35. Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567
36. Dai, J.-J.; Fang, C.; Xiao, B.; Yi, J.; Xu, J.; Liu, Z.-J.; Lu, X.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 8436
37. Mizuta, S.; Verhoog, S.; Wang, X.; Shibata, N.; Gouverneur, V.; Médebielle, M. J. Fluorine Chem. 2013, 155, 124
38. Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300
39. Haynes, W. M.; Lide, D. R.; Bruno, T. J. CRC Handbook of Chemistry and Physics, 93 rd ed.; Taylor & Francis: New York, 2012.
40. Catalán, J.; Díaz, C.; López, V.; Pérez, P.; Paz, J. -L. G.; Rodríguez, J. G. Liebigs. Ann. Chem. 1996, 1785