Axially chiral C 2-symmetric N-heterocyclic carbene (NHC) palladium complex-catalyzed asymmetric fluorination and amination of oxindoles

Chinese Journal of Chemistry

Volumn 30, Issue 6, 2012, Pages 1295-1304

  Zhang, Rui ^a   Wang, De ^a   Xu, Qin ^a   Jiang, Jiajun ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

(S) BINAM; 1 chloromethyl 4 fluoro 1,4 diazoniabicyclo 2. 2.2 octane bis(tetrafluoroborate) (selectfluor); asymmetric fluorination of oxindoles; chiral C 2 symmetric N heterocyclic carbene (NHC) palladium diaquo complex; N fluorobenzenesulfonimide (NFSI)

Indexed keywords

EID: 84862572887     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201200289     Document Type: Article

References (62)

1. Kirsch, P., Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
2. Filler, R.; Kobayashi, Y., In Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Ed.:, Yagupolskii, L. M., Elsevier, Amsterdam, 1993.
3. Uneyama, K., Organofluorine Chemistry, Blackwell, Oxford, 2006.
4. Thayer, A. M.,. Chem. Eng. News, 2006, 84, 15.
5. Chambers, R. D., Fluorine in Organic Chemistry, Blackwell, Oxford, 2004.
6. Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M., In Organofluorine Compounds: Chemistry and Applications, Springer-Verlag, Berlin, 2000.
7. Kirk, K. L.,. J. Fluorine Chem., 2006, 127, 1013.
8. Isanbor, C.; O'Hagan, D.,. J. Fluorine Chem., 2006, 127, 303.
9. Ma, J.; Cahard, D.,. Chem. Rev., 2004, 104, 6119.
10. Müller, K.; Faeh, C.; Diederich, F.,. Science, 2007, 317, 1881.
11. Hagmann, W. K.,. J. Med. Chem., 2008, 51, 4359.
12. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V.,. Chem. Soc. Rev., 2008, 37, 320.
13. Hintermann, L.; Togni, A.,. Angew. Chem., Int. Ed., 2000, 39, 4359.
14. Ibrahim, H.; Togni, A.,. Chem. Commun., 2004, 1147.
15. Lectard, S.; Hamashima, Y.; Sodeoka, M.,. Adv. Synth. Catal., 2010. 352, 2708.
16. Shibata, N.; Suzuki, E.; Takeuchi, Y.,. J. Am. Chem. Soc., 2000, 122, 10728.
17. Shibata, N.; Suzuki, E.; Asahi, T.; Shiro, M.,. J. Am. Chem. Soc., 2001, 123, 7001.
18. Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K. L.,. J. Org. Chem., 2003, 68, 2494.
19. Shibata, N.; Ishimaru, T.; Nakamura, M.; Toru, T.,. Synlett, 2004, 2509.
20. Shibata, N.; Ishimaru, T.; Nagai, T.; Kohno, J.; Toru, T.,. Synlett, 2004, 1703.
21. Fukuzumi, T.; Shibata, N.; Sugiura, M.; Nakamura, S.; Toru, T.,. J. Fluorine Chem., 2006, 127, 548.
22. Shibata, N.; Yasui, H.; Nakamura, S.; Toru, T.,. Synlett, 2007, 1153.
23. Reddy, D. S.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S.,. Angew. Chem., Int. Ed., 2008, 47, 164.
24. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M.,. Angew. Chem., Int. Ed., 2008, 47, 4157.
25. Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M.,. J. Am. Chem. Soc., 2002, 124, 14530.
26. Frantz, R.; Hintermann, L.; Perseghini, M.; Broggini, D.; Togni, A.,. Org. Lett., 2003, 5, 1709.
27. Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M.,. Org. Lett., 2003, 5, 3225.
28. Toullec, P. Y.; Bonaccorsi, C.; Mezztti, A.; Togni, A.,. Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 5810.
29. Ma, J.-A.; Cahard, D.,. Tetrahedron: Asymmetry, 2004, 15, 1007.
30. Kim, H. R.; Kim, D. Y.,. Tetrahedron Lett., 2005, 46, 3115.
31. Bernardi, L.; Jøgensen, K. A.,. Chem. Commun., 2005, 1324.
32. Perseghini, M.; Massaccesi, M.; Liu, Y.; Togni, A.,. Tetrahedron, 2006, 62, 7180.
33. Bonaccorsi, C.; Althaus, M.; Becker, C.; Togni, A.; Mezzetti, A.,. Pure Appl. Chem., 2006, 78, 391.
34. Kim, S. M.; Kang, Y. K.; Lee, K. S.; Mang, J. Y.; Kim, D. Y.,. Bull. Korean Chem. Soc., 2006, 27, 423.
35. Suzuki, S.; Furuno, H.; Yokoyama, Y.; Inanaga, J.,. Tetrahedron: Asymmetry, 2006, 17, 504.
36. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Tsuchiya, Y.; Moriya, K.; Goto, T.; Sodeoka, M.,. Tetrahedron, 2006, 62, 7168.
37. Althaus, M.; Becker, C.; Togni, A.; Mezzetti, A.,. Organometallics, 2007, 26, 5902.
38. Suzuki, T.; Goto, T.; Hamashima, Y.; Sodeoka, M.,. J. Org. Chem., 2007, 72, 246.
39. Shibatomi, K.; Tsuzuki, Y.; Nakata, S.; Sumikawa, Y.; Iwasa, S.,. Synlett, 2007, 551.
40. Kang, K.; Cho, M. J.; Kim, S. M.; Kim, D. Y.,. Synlett, 2007, 1135.
41. Moriya, K.; Hamashima, Y.; Sodeoka, M.,. Synlett, 2007, 1139.
42. Enders, D.; Hüttl, M. R. M.,. Synlett, 2005, 991.
43. Marigo, M.; Fielenbach, D.; Braunton, A.; Kjasgaard, A.; Jøgensen, K. A.,. Angew. Chem., Int. Ed., 2005, 44, 3703.
44. Steiner, D. D.; Mase, N.; Barbas III, C. F.,. Angew. Chem., Int. Ed., 2005, 44, 3706.
45. Beeson, T. D.; MacMillan, D. W. C.,. J. Am. Chem. Soc., 2005, 127, 8826.
46. Shibatomi, K.; Yamamoto, H.,. Angew. Chem., Int. Ed., 2008, 47, 5796.
47. Brandes, S.; Niess, B.; Bella, M.; Prieto, A.; Overgaard, J.; Jøgensen, K. A.,. Chem. Eur. J., 2006, 12, 6039.
48. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M.,. J. Am. Chem. Soc., 2005, 127, 10164.
49. Xu, Q.; Duan, W. L.; Lei, Z. Y.; Zhu, Z. B.; Shi, M.,. Tetrahedron, 2005, 61, 11225.
50. Chen, T.; Jiang, J. J.; Xu, Q.; Shi, M.,. Org. Lett., 2007, 9, 865.
51. Zhang, T.; Shi, M.,. Chem. Eur. J., 2008, 14, 3759.
52. Ma, G. N.; Zhang, T.; Shi, M.,. Org. Lett., 2009, 11, 875.
53. Wang, W. F.; Zhang, T.; Shi, M.,. Organometallics, 2009, 28, 2640.
54. Liu, Z.; Shi, M.,. Tetrahedron, 2010, 66, 2619.
55. Liu, Z.; Shi, M.,. Organometallics, 2010, 29, 2831.
56. Xu, Q.; Zhang, R.; Zhang, T.; Shi, M.,. J. Org. Chem., 2010, 75, 3935.
57. Zhang, R.; Xu, Q.; Zhang, X.; Zhang, T.; Shi, M.,. Tetrahedron: Asymmetry, 2010, 21, 1928.
58. Wang, W.; Zhang, T.; Wang, F.; Shi, M.,. Tetrahedron, 2011, 67, 1523.
59. Liu, Z.; Gu, P.; Shi, M.,. Org. Lett., 2011, 13, 2314.
60. Liu, Z.; Gu, P.; Shi, M.,. Chem. Eur. J., 2011, 17, 5796.
61. Wang, W.; Yang, J.; Wang, F.; Shi, M.,. Organometallics, 2011, 30, 3859.
62. Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.; Nakamura, S.; Toru, T.; Kanemasa, S.,. Angew. Chem., Int. Ed., 2005, 44, 4204.