The scope and limitation of nickel-catalyzed aminocarbonylation of aryl bromides from formamide derivatives

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6358-6361

  Jo, Youngshin ^a   Ju, Jinhun ^a   Choe, Jaehoon ^b   Kwang, Ho Song ^c   Lee, Sunwoo ^a  

^a Chonnam National University   (South Korea)

^b LG Chemical Ltd   (South Korea)

^c Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ARYL AMIDE; ARYL BROMIDES; ARYL HALIDES; CATALYTIC LOADING; CATALYTIC SYSTEM; CHEMICAL EQUATIONS; FORMAMIDES; GOOD YIELD; HIGHER YIELD;

AMIDES; BROMINE COMPOUNDS; CHEMICAL REACTIONS; NICKEL ALLOYS;

NICKEL;

BROMIDE; FORMAMIDE DERIVATIVE; NICKEL; PHOSPHITE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL ANALYSIS;

EID: 70349101645     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901065y     Document Type: Article

References (36)

1. (a) Pradhan, K. J.; Variyar, P. S.; Bandekar, J. R.; Lebensm, Wiss. U. Technology 1999, 32, 121-123.
2. (b) Aki-Sener, E.; Bingol,K.K.; Oren, I.; Temiz- Arpaci,O.; Yalcin, I.; Altanlar,N. Farmaco 2000, 55, 469-476.
3. (c)Kobayashi, I.; Muraoka, H.; Hasegawa, M.; Saika, T.; Nishida, M.; Kawamura, M.; Ando, R. J. Antimicrob. Chemother. 2002, 50, 129-132.
4. (d) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
5. (a) Ishihara, K.; Yano, T. Org. Lett. 2004, 6, 1983-1986.
6. (b) Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Kantam, M. L. Eur. J. Org. Chem. 2008, 3619-3622.
7. (c) Chang, J. W. W.; Chan, P. W. H. Angew. Chem., Int. Ed. 2008, 47, 1138-1140.
8. (d) Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 13796-13797.
9. (e) Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798-13799.
10. (f) Ekoue-Kovi, K.; Wolf, C. Org. Lett. 2007, 9, 3429-3432.
11. (g) Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 790.
12. (h) Li, J.; Xu, F.; Zhang, Y.; Shen, Q. J. Org. Chem. 2009, 74, 2575-2577.
13. (a) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331.
14. (b) Soderberg, B. C. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; Vol.12, pp 249-251.
15. (c) Tsuji, J. Palladium Reagents and Catalysis; Wiley: Chichester, UK, 1995; pp 196-198.
16. (d) Colguhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum: New York, 1991; pp 145-149.
17. (a) Beller, M.; Indolese, A. F. Chimia 2001, 55, 684-687.
18. (b) Skoda- Foldes, R.; Kollar, L. Curr. Org. Chem. 2002, 6, 1097-1119.
19. (a) Kaiser, N. F. K.; Hallberg, A.; Larhed, M. J. Comb. Chem. 2002, 4, 109-111.
20. (b) Georgsson, J.; Harberg, A.; Larhded, M. J. Comb. Chem. 2003, 5, 350-352.
21. (c) Wannberg, J.; Larhed, M. J. Org. Chem. 2003, 68, 5750-5753.
22. (d) Wu, X.; Ekegren, J. K.; Larhed, M. Organometallics 2006, 25, 1434-1439.
23. (e) Wu, X.; Wannberg, J.; Larhed, M. Tetrahedron 2006, 62, 4665-4670.
24. Lindsay, C. M.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1988, 569-573.
25. (a) Cunico, R. F.; Maity, B. C. Org. Lett. 2002, 4, 4357-4359.
26. (b) Cunico, R. F.; Maity, B. C. Org. Lett. 2003, 5, 4947-4949.
27. (c) Cunico, R. F.; Pandey, R. K. J. Org. Chem. 2005, 70, 9048-9050.
28. (a) Rusina, A.; Vlcek, A. A. Nature 1965, 206, 295-296.
29. (b) Serp, P.; Hernandez, M.; Richard, B.; Kalck, P. Eur. J. Inorg. Chem. 2001, 2327-2336.
30. Wan, Y.; Alterman, M.; Larhed, M.; Hallbeg, A. J. Org. Chem. 2002, 67, 6232-6235.
31. Hosoi, K.; Nozaki, K.; Hiyama, T. Org. Lett. 2002, 4, 2849-2851.
32. Ju, J.; Jeong, M.; Moon, J.; Jung, H. M.; Lee, S. Org. Lett. 2007, 9, 4615-4618.
33. The basicity of potassium methoxide is greater than that of sodium methoxide.
34. For Pd-catalyzed N-arylation of formamides, see: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
35. For Cu-catalyzed N-arylation of formamides, see: (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
36. Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 5070-5071.