Ni(II)-(σ-aryl) complex: A facile, efficient catalyst for nickel-catalyzed carbon-nitrogen coupling reactions

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6324-6327

  Chen, Chen ^a,b   Yang, Lian Ming ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CATALYSTS; CHLORINE COMPOUNDS; LIGANDS; REACTION KINETICS;

CARBON-NITROGEN COUPLING REACTIONS; N-HETEROCYCLIC CARBENE LIGANDS;

NICKEL COMPOUNDS;

ANILINE DERIVATIVE; CARBENOID; CARBON; NICKEL COMPLEX; NITROGEN; PHOSPHINE DERIVATIVE;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; REACTION ANALYSIS; SYNTHESIS;

EID: 34547647849     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0709448     Document Type: Article

References (56)

1. For the Heck reaction, see: (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 14, 2320-2322.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
3. For the Sonogashira reaction, see: (a) Beletskaya, I. P.; Latyshev, G. V.; Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44, 5011-5013.
4. (b) Wang, L.; Li, P.; Zhang, Y. Chem. Commun. 2004, 514-515.
5. For the Still reaction, see: (a) Kosugi, M.; Fugami, K. J. Organomet. Chem. 2002, 653, 50-53.
6. (b) Shirakawa, E.; Yamasaki, K.; Hiyama, T. J. Chem. Soc., Perkin Trans. 1 1997, 2449-2450.
7. (c) Kang, S.; Ryu, H.; Lee, S. J. Chem. Soc., Perkin Trans. 1 1999, 2661-2663.
8. For the Ullmann reaction, see: (a) Takagi, K.; Hayama, N.; Inokawa, S. Bull. Chem. Soc. Jpn. 1980, 53, 3691-3695.
9. (b) Takagi, K.; Hayama, N. Chem. Lett. 1983, 12, 637-638.
10. (c) Lin, G. Q.; Hong, R. J. Org. Chem. 2001, 66, 2877-2880.
11. For the Kumada-Corriu reaction, see: (a) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374-4376.
12. (b) Corriu, R. J. P.; Masse, J. P. Chem. Commun. 1972, 144.
13. (c) Bohm, V. P. W.; Weskamp, T.; Gstottmayr, C. W. K.; Hermann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602-1604.
14. (d) Terao, J.; Watanabe, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 3656-3657.
15. (e) Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem. Soc 2005, 127, 17978-17979.
16. For the Negishi reaction, see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320.
17. (b) Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Org. Lett. 2005, 7, 4871-4874.
18. (c) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819-5820.
19. For the Suzuki reaction, see: (a) Percec, V.; Bae, J-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065.
20. (b) Galland, J.-C.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 1999, 40, 2323-2326.
21. (c) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993-2996.
22. (d) Saito, S.; Oh-tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024-8030.
23. (e) Tang, Z.-Y.; Hu, Q.-S. J. Org. Chem. 2006, 71, 2167-2169.
24. (f) Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513-3516.
25. (g) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8657-8660.
26. (h) Zim, D.; Lando, V. R.; Dupont, J.; Monterio, A. L. Org. Lett. 2001, 3, 3049-3051.
27. (i) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447-3452.
28. (j) Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139-2144.
29. (a) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058.
30. (b) Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 7, 911-913.
31. (c) Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492-4494.
32. (d) Brenner, E.; Fort, Y. Tetrahedron Lett. 1998, 39, 5359-5362.
33. (e) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829-12842.
34. (f) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875-2879.
35. (g) Gradel, B.; Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 5689-5692.
36. (h) Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029-3036.
37. For comprehensive reviews on Pd-catalyzed cross-coupling reactions, see: (a) Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley & Sons: New York, 2004.
38. (b) Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219
39. Fu, G. C.; Littke, A. F. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
40. iPr) for C-C coupling; see: Leadbeater, N. E. J. Org. Chem. 2001, 66, 7539-7541.
41. (a) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547-7560.
42. (b) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319-6332.
43. (c) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262-7270.
44. (d) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366.
45. (e) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267-2273.
46. (a) For a successful example of the Ni(II)-(σ-aryl) complex catalyzed cyanation of bromothiophene, see: Soolinger, J. V.; Verkruijsse, H. D.; Keegstra, M. A.; Brandsma, L. Synth. Commun. 1990, 20, 3153-3156.
47. (b) Most recently we used Ni(II)-(σ-aryl) complexes as catalysts in the Suzuki reaction: Chen, C.; Yang, L. M. Tetrahedron Lett. 2007, 48, 2427-2430.
48. For the preparation of nickel-(σ-aryl) complexes, see: (a) Cassar, L.; Ferrara, S.; Foá, M. Advances in Chemistry Series; American Chemical Society: Washington, DC, 1974; Vol. 132, p 252.
49. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: New York, 1998; pp 3-4.
50. Two imidazolium salts were chosen: 1,3-bis(2,6-diisopropylphenyl)- imidazolium chloride (IPr·HCl) and 1,3-bis(2,6-diisopropylphenyl) dihydroimidazolium chloride (SIPr·HCl). For their preparation, see: (a) Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523-14534.
51. (b) Grasa, G. A.; Viciu, M. S.; J. Huang; Nolan, S. P. J. Org. Chem. 2001, 66, 7729-7737.
52. (a) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668-3671.
53. (b) Bedford, R. B.; Cazin, J. C. S.; Hazelwook, S. L. Chem.Commun. 2002, 22, 2608-2609.
54. (c) Spencer, J.; Sharratt, D. P.; Dupont, J.; Monteiro, A. L.; Reis, V. I.; Stracke, M. P.; Rominger, F.; McDonald, I. M. Organometallics 2005, 24, 5665-5672.
55. (a) Lee, C. C.; Ke, W. C.; Chan, K. T.; Lai, C. L.; Hu, C. H.; Lee, H. M. Chem. Eur. J. 2006, 13, 582-591.
56. (b) Ho, C. Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782-785.