Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation with Boronic Acids, Aryl Diazonium Ions, and Ammonia

Synthesis

Volumn , Issue 18, 2003, Pages 2886-2889

  Ma, Yudao ^a   Song, Chun ^b   Chai, Qiang ^c   Ma, Changqin ^a   Andrus, Merritt B ^b  

^a SHANDONG UNIVERSITY   (China)

^b Brigham Young University   (United States)

^c SHANDONG PROVINCIAL HOSPITAL AFFILIATED TO SHANDONG FIRST MEDICAL UNIVERSITY   (China)

Author keywords

Amides; Carbonylative coupling; Multi component; N heterocyclic carbene; Palladium cross coupling

Indexed keywords

AMMONIA; CATALYSIS; CATALYSTS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

LIGANDS;

AROMATIC COMPOUNDS;

AMIDE; AMMONIA; BORONIC ACID DERIVATIVE; CARBENE; CARBON MONOXIDE; DIAZONIUM COMPOUND; IMIDAZOLE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMIDATION; ANALYTIC METHOD; ARTICLE; ARYLATION; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OXYGEN SATURATION;

EID: 0346690003     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42478     Document Type: Article

References (40)

1. (a) Ritter, K. Synthesis 1993, 735.
2. (b) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318.
3. (c) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
4. (d) Gavino, R.; Pellegrini, S.; Castenet, Y.; Mortreux, A.; Mentre, O. Appl. Catal. A 2001, 217, 91.
5. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557.
6. (b) Ceccarelli, S.; Piarulli, U.; Gennari, C.J. Org. Chem. 2000, 65, 6254.
7. (a) Ishiyama, T.; Kizaki, H.; Suzuki, A.; Miyaura, N. Tetrahedron Lett. 1993, 34, 7595.
8. (b) Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726.
9. (c) Skoda-Földes, R.; Székvölgi, Z.; Kollár, L.; Berente, Z.; Horváth, J.; Tuba, Z. Tetrahedron 2000, 56, 3415.
10. Iwata, T.; Miyake, Y.; Nishibayashi, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2002, 1548.
11. Yamamoto, M.; Kohara, T.; Yamamoto, A. Chem. Lett. 1976, 1217.
12. Bumagin, N. A.; Ponomaryov, A. B.; Beletskaya, I. P. Tetrahedron Lett. 1985, 26, 4819.
13. Hatanaka, Y.; Fukushima, S.; Hiyama, T. Tetrahedron 1992, 48, 2113.
14. (a) Kang, S.-K.; Kim, W.-Y.; Lee, Y.-T.; Ahn, S.-K.; Kim, J.-C. Tetrahedron Lett. 1998, 39, 2131.
15. (b) Kang, S.-K.; Lim, K.-H.; Ho, P.-S.; Yoon, S.-K.; Son, H.-J. Synth. Commun. 1998, 28, 1481.
16. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
17. (b) Hua, D. H.; Takasu, K.; Huang, X.; Millward, G. S.; Chen, Y.; Fan, J. Tetrahedron 2000, 56, 7389.
18. (a) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
19. (b) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042.
20. (a) Tanaka, M.; Kobayashi, T.; Sakakura, T. J. Chem. Soc. Jpn. 1985, 537.
21. (b) Kiji, J.; Okano, T.; Kimura, H.; Saiki, K. J. Mol. Catal. A: Chem. 1998, 130, 95.
22. Nishiyama, Y.; Tokunaga, K.; Kawamatsu, H.; Sonoda, N. Tetrahedron Lett. 2002, 43, 1507.
23. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
24. (b) Georgsson, J.; Hallberg, A.; Larhed, M. J. Comb. Chem. 2003, 5, 350.
25. Carpentier, J.-F.; Castanet, Y.; Brocard, J.; Mortreux, A.; Petit, F. Tetrahedron Lett. 1991, 32, 4705.
26. Morimoto, T.; Fujioka, M.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. Chem. Lett. 2003, 32, 154.
27. Andrus, M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137.
28. (a) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
29. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
30. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371.
31. (b) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
32. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
33. (b) Fürstner, A.; Leitner, A. Synlett 2001, 290.
34. (c) Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
35. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
36. (a) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
37. (b) Bölm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrman, W. A. Angew. Chem. Int. Ed. 2000, 39, 1602.
38. (a) Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761.
39. (b) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079.
40. (c) Ma, Y.; Song, C.; Jiang, W.; Xue, G.; Cannon, J. F.; Wang, X.; Andrus, M. B. Org. Lett. 2003, in press.