Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3316-3319

  Nakamura, Yuki ^a   Yoshikai, Naohiko ^a,b   Ilies, Laurean ^a   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROBENZENE; LIGAND; NICKEL; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; FLUOROBENZENES; LIGANDS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; STEREOISOMERISM; ZINC;

EID: 84863611879     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301195x     Document Type: Article

References (55)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
2. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250
3. Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107, 1066-1096
4. Badudri, F.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003-1022
5. Burton, D. J. Tetrahedron 1992, 48, 189-275
6. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555-6666
7. Maggiarosa, N.; Tyrra, W.; Naumann, D.; Kirij, N. V.; Yagupolskii, Y. L. Angew. Chem., Int. Ed. 1999, 38, 2252-2253
8. Prakash, G. K. S.; Mandal, M. J. Fluorine Chem. 2001, 112, 123-131
9. Deacon, G. B.; Forsyth, C. M.; Sun, J. Tetrahedron Lett. 1994, 35, 1095-1098
10. Adonin, N. Y.; Starichenko, V. F. J. Fluorine Chem. 2000, 101, 65-67
11. Laev, S. S.; Evtefeev, V. U.; Shteingarts, V. D. J. Fluorine Chem. 2001, 110, 43-46
12. Miller, A. O.; Krasnov, V. I.; Peters, D.; Platonov, V. E.; Miethchen, R. Tetrahedron Lett. 2000, 41, 3817-3819
13. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119-2183
14. Richmond, T. G. Angew. Chem., Int. Ed. 2000, 39, 3241-3244
15. Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431
16. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1973, 50, C12-C14
17. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969
18. Saeki, T.; Takashima, Y.; Tamao, K. Synlett 2005, 11, 1771-1774
19. Ohashi, M.; Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256-3259
20. Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964-15965
21. Wang, T.; Alfonso, B. J.; Love, J. A. Org. Lett. 2007, 9, 5629-5631
22. Wang, T.; Love, J. A. Organometallics 2008, 27, 3290-3296
23. Sun, A. D.; Love, J. A. Org. Lett. 2011, 13, 2750-2753
24. Manabe, K.; Ishikawa, S. Synthesis 2008, 16, 2645-2649
25. Wang, J.-R.; Manabe, K. Org. Lett. 2009, 11, 741-744
26. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263
27. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319
28. Osakada, K.; Onodera, H.; Nishihara, Y. Organometallics 2005, 24, 190-192
29. Shekhar, S.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 13016-13027
30. Koizumi, T.; Yamazaki, A.; Yamamoto, T. Dalton Trans. 2008, 3949-3952
31. Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15258-15259
32. Strawser, D.; Karton, A.; Zenkina, O. V.; Iron, M. A.; Shimon, L. J. W.; Martin, J. M. L.; van der Boom, M. E. J. Am. Chem. Soc. 2005, 127, 9322-9323
33. Iverson, C. N.; Lachicotte, R. J.; Müller, C.; Jones, W. D. Organometallics 2002, 21, 5320-5333
34. Carbó, J. J.; Eisenstein, O.; Higgitt, C. L.; Klahn, A. H.; Maseras, F.; Oelckers, B.; Perutz, R. N. J. Chem. Soc., Dalton Trans. 2001, 1452-1461
35. Bach, I.; Pörschke, K.-R.; Goddard, R.; Kopiske, C.; Krüger, C.; Rufínska, A.; Seevogel, K. Organometallics 1996, 15, 4959-4966
36. Böhm, V. P. W.; Grötmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387-3389
37. Ackermann, L.; Born, R.; Spatz, J. H.; Meyer, D. Angew. Chem., Int. Ed. 2005, 44, 7216-7219
38. Mongin, F.; Mojovic, L.; Giullamet, B.; Trécourt, F.; Quéguiner, G. J. Org. Chem. 2002, 67, 8991-8994
39. Dankwardt, J. E. J. Organomet. Chem. 2005, 690, 932-938
40. Inamoto, K.; Kuroda, J.; Sakamoto, T.; Hiroya, K. Synthesis 2007, 18, 2853-2861
41. Schaub, T.; Fischer, P.; Steffen, A.; Braun, T.; Radius, U.; Mix, A. J. Am. Chem. Soc. 2008, 130, 9304-9317
42. Ackermann, L.; Wechsler, C.; Kapdi, A.; Althammer, A. Synlett 2010, 2, 294-298
43. Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 17978-17979
44. Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 9590-9599
45. Yoshikai, N.; Nakamura, E. Chem. Rev. 2012, 112, 2339-2372
46. Mori, S.; Nakamura, E. THEOCHEM 1999, 461-462, 167-175
47. Zenkina, O. V.; Karton, A.; Freeman, D.; Shimon, L. J. W.; Martin, J. M. L.; van der Boom, M. E. Inorg. Chem. 2008, 47, 5114-5121
48. Jin, L.; Liu, C.; Liu, J.; Hu, F.; Lan, Y.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B.; Lei, A. J. Am. Chem. Soc. 2009, 131, 16656-16657
49. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858-5859
50. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925-2928
51. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Synlett 2010, 313-316
52. Aizenberg, M.; Milstein, D. Science 1994, 265, 359-361
53. Guo, H.; Kong, F.; Kanno, K.; He, J.; Nakajima, K.; Takahashi, T. Organometallics 2006, 25, 2045-2048
54. Selander, N.; Szabó, K. J. Chem. Rev. 2011, 111, 2048-2076
55. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759-1792