Convenient palladium-catalyzed aminocarbonylation of anilines to N-arylbenzamides

Tetrahedron Letters

Volumn 52, Issue 29, 2011, Pages 3702-3704

  Wu, Xiao Feng ^a   Schranck, Johannes ^a   Neumann, Helfried ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amides; Anilines; Carbonylation; Diazotization; Palladium

Indexed keywords

ANILINE; BENZAMIDE DERIVATIVE; HEPTANE; LIGAND; PALLADIUM ACETATE; SOLVENT;

AMIDATION; ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; DIAZOTIZATION; LOW TEMPERATURE; REACTION ANALYSIS;

EID: 79959222533     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.111     Document Type: Article

References (47)

1. For selected reviews see: (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047-3101;
2. (b) Rollet, P.; Kleist, W.; Dufaud, V.; Djakovitch, L. J. Mol. Catal. 2005, 241, 39-51;
3. (c) Zapf, A.; Beller, M. Chem. Commun. 2005, 431-440;
4. (d) Frisch, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688;
5. (e) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017;
6. (f) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361;
7. (g) Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871;
8. (h) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489;
9. (i) Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027-3043;
10. (j) Zapf, A.; Beller, M. Top. Catal. 2002, 19, 101-109;
11. (k) Tucker, C. E.; de Vries, J. G. Top. Catal. 2002, 19, 111-118.
12. Wu, X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047-9050.
13. For reviews on palladium-catalyzed carbonylations see: (a) Grigg, R.; Mutton, S. P. Tetrahedron 2010, 66, 5515-5548;
14. (b) Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133;
15. (c) Brennführer, A.; Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28-41;
16. (d) Skoda-Földes, R.; Kollár, L. Curr. Org. Chem. 2002, 6, 1097-1119;
17. (e) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A: Chem. 1995, 104, 17-85.
18. Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622-4643.
19. (a) Nagira, K.; Kikukawa, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1980, 45, 2365-2368;
20. (b) Kikukawa, K.; Kono, K.; Nagira, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1981, 46, 4413-4416;
21. (c) Kikukawa, K.; Kono, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron Lett. 1980, 21, 2877-2878.
22. Siegrist, U.; Rapold, T.; Blaser, H. Org. Process Res. Dev. 2003, 7, 429-431.
23. Sengupta, S.; Sadhukhan, S. K.; Bhattacharyya, S.; Guha, J. J. Chem. Soc., Perkin Trans. 1 1998, 407-410.
24. (a) Kikikawa, K.; Totoki, T.; Wada, F.; Matsuda, T. J. Organomet. Chem. 1984, 270, 283-287;
25. (b) Herr, R. J.; Fairfax, D. J.; Meckler, H.; Wilson, J. D. Org. Process Res. Dev. 2002, 6, 677-681.
26. (a) Kikukawa, K.; Idemoto, T.; Katayama, A.; Kono, K.; Wada, F.; Matsuda, T. J. Chem. Soc., Perkin Trans. 1 1987, 1511-1514;
27. (b) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. Chem. Lett. 1982, 35-36.
28. Andrus, M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137-9140.
29. Ma, Y.; Song, C.; Chai, Q.; Ma, C.; Andrus, M. B. Synthesis 2003, 2886-2889.
30. (a) Wu, X.-F.; Neumann, H.; Beller, M. ChemCatChem 2010, 2, 509-513;
31. (b) Wu, X. -F.; Neumann, H.; Beller, M. Chem. Eur. J. 2010, 16, 9750-9753;
32. (c) Wu, X. -F.; Neumann, H.; Beller, M. Chem. Asian J. 2010, 5, 2168-2172;
33. (d) Wu, X.-F.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 5284-5288;
34. (e) Wu, X. -F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 7316-7319;
35. (f) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Eur. J. 2010, 16, 12104-12107;
36. (g) Wu, X.-F.; Neumann, H.; Beller, M. Tetrahedron Lett. 2010, 51, 6146-6149;
37. (h) Wu, X.-F.; Neumann, H.; Spannenberg, A.; Schulz, T.; Jiao, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 14596-14602;
38. (i) Wu, X.-F.; Sundararaju, B.; Neumann, H.; Dixneuf, P. H.; Beller, M. Chem. Eur. J. 2011, 17, 106-110;
39. (j) Wu, X.-F.; Neumann, H.; Beller, M. Adv. Synth. Catal. 2011, 353, 788-792;
40. (k) Wu, X.-F.; Jiao, H.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 726-733.
41. See for examples: N-aryl amides; The Merck Index, 11th ed., Merck, Rahway, USA, 1989.
42. 3): δ 165.5, 139.1, 134.9, 131.5, 128.6, 128.3, 127.6, 123.6, 120.3. GC-MS (EI, 70eV): m/z (%) = 197 (M+, 60), 105 (100), 77 (40).
43. For selected examples on palladium-catalyzed aminocarbonylation of aryl halides see: (a) Martinelli, J. R.; Clark, T. P.; Watson, D. A.; Munday, R. H.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 8460-8463;
44. (b) Tambade, P. J.; Patil, Y. P.; Bhanage, B. M. Appl. Organomet. Chem. 2009, 23, 235-240;
45. (c) Szilágyi, A.; Farkas, R.; Petz, A.; Kollár, L. Tetrahedron 2009, 65, 4484-4489;
46. (d) Salvadori, J.; Balducci, E.; Zaza, S.; Petricci, E.; Taddei, M. J. Org. Chem. 2010, 75, 1841-1847;
47. (e) Martinelli, J. P.; Watson, D. A.; Freckmann, D. M. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7102-7107.