Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct C - H Bond Functionalization

Angewandte Chemie - International Edition

Volumn 54, Issue 15, 2015, Pages 4669-4672

  Xu, Shuai ^a   Wu, Guojiao ^a   Ye, Fei ^a   Wang, Xi ^a   Li, Huan ^a   Zhao, Xia ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

C H activation; carbenes; copper; diazo compounds; synthetic methods

Indexed keywords

ACTIVATION ANALYSIS; ALKYLATION; CATALYSIS; ORGANIC COMPOUNDS;

C-H ACTIVATION; C-H BOND FUNCTIONALIZATION; CARBENES; DIAZO COMPOUNDS; ELECTRON-DEFICIENT; MIGRATORY INSERTION; REACTION PATHWAYS; SYNTHETIC METHODS;

COPPER;

AROMATIC HYDROCARBON; AZO COMPOUND; CARBENE; COPPER; FLUORINE; HYDRAZONE DERIVATIVE; METHANE; TOLUENESULFONIC ACID DERIVATIVE;

ALKYLATION; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; ELECTRON; HALOGENATION; SYNTHESIS;

ALKYLATION; AZO COMPOUNDS; CATALYSIS; COPPER; ELECTRONS; FLUORINE; HALOGENATION; HYDRAZONES; HYDROCARBONS, AROMATIC; METHANE; TOSYL COMPOUNDS;

EID: 84926379666     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201412450     Document Type: Article

References (45)

1. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 2003, 42, 1210
2. Angew. Chem. 2003, 115, 1244
3. K. Muller, C. Faeh, F. Diederich, Science 2007, 317, 1881
4. A. R. Murphy, J. M. J. Fréchet, Chem. Rev. 2007, 107, 1066
5. F. Babudri, G. M. Farinola, F. Naso, R. Ragni, Chem. Commun. 2007, 1003
6. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
7. H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119
8. T. Ahrens, J. Kohlmann, M. Ahrens, T. Braun, Chem. Rev. 2015, 115, 931.
9. R. J. Harper, Jr., E. J. Soloski, C. Tamborski, J. Org. Chem. 1964, 29, 2385
10. T. Korenaga, T. Kosaki, R. Fukumura, T. Ema, T. Sakai, Org. Lett. 2005, 7, 4915
11. A. C. Albéniz, P. Espinet, B. Martín-Ruiz, D. Milstein, J. Am. Chem. Soc. 2001, 123, 11504
12. A. C. Albéniz, P. Espinet, B. Martín-Ruiz, D. Milstein, Organometallics 2005, 24, 3679
13. R. Shang, Y. Fu, Y. Wang, Q. Xu, H. Z. Yu, L. Liu, Angew. Chem. Int. Ed. 2009, 48, 9350
14. Angew. Chem. 2009, 121, 9514
15. R. Shang, Q. Xu, Y. Y. Jiang, Y. Wang, L. Liu, Org. Lett. 2010, 12, 1000.
16. M. Lafrance, C. N. Rowley, T. K. Woo, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 8754
17. M. Lafrance, D. Shore, K. Fagnou, Org. Lett. 2006, 8, 5097.
18. H. Q. Do, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 1128
19. H.-Q. Do, R. M. K. Khan, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 15185.
20. C. Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010, 132, 12850
21. Y. Wei, W. Su, J. Am. Chem. Soc. 2010, 132, 16377.
22. S. Fan, F. Chen, X. Zhang, Angew. Chem. Int. Ed. 2011, 50, 5918
23. Angew. Chem. 2011, 123, 6040
24. G. W. Wang, A.-X. Zhou, S.-X. Li, S.-D. Yang, Org. Lett. 2014, 16, 3118.
25. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522.
26. X. Zhang, S. Fan, C. Y. He, X. Wan, Q. Q. Min, J. Yang, Z. X. Jiang, J. Am. Chem. Soc. 2010, 132, 4506
27. C. Z. Wu, C. Y. He, Y. G. Huang, X. Zhang, Org. Lett. 2013, 15, 5266.
28. Y. Nakao, N. Kashihara, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 16170.
29. N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2358
30. T. Yao, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2011, 50, 2990
31. Angew. Chem. 2011, 123, 3046
32. A. Nakatani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2012, 14, 2586.
33. T. Hatakeyama, Y. Kondo, Y. i. Fujiwara, H. Takaya, S. Ito, E. Nakamura, M. Nakamura, Chem. Commun. 2009, 1216.
34. S. Fan, C. Y. He, X. Zhang, Chem. Commun. 2010, 46, 4926.
35. Z.-M. Sun, J. Zhang, R. S. Manan, P. Zhao, J. Am. Chem. Soc. 2010, 132, 6935.
36. Q. Xiao, Y. Xia, H. Li, Y. Zhang, J. Wang, Angew. Chem. Int. Ed. 2011, 50, 1114
37. Angew. Chem. 2011, 123, 1146
38. F. Ye, X. Ma, Q. Xiao, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2012, 134, 5742.
39. X. Zhao, G. Wu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 3296.
40. Q. Xiao, L. Ling, F. Ye, R. Tan, L. Tian, Y. Zhang, Y. Li, J. Wang, J. Org. Chem. 2013, 78, 3879.
41. A. V. Babkov, Polyhedron 1988, 7, 1203.
42. D. F. Duxbury, Chem. Rev. 1993, 93, 381.
43. M. Terrier, T. Boubaker, L. Xiao, P. G. Farrell, J. Org. Chem. 1992, 57, 3924
44. M. R. Detty, S. L. Gibson, S. J. Wagner, J. Med. Chem. 2004, 47, 3897.
45. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998.