Iron-catalyzed N-arylations of amides

Chemistry - A European Journal

Volumn 14, Issue 12, 2008, Pages 3527-3529

  Correa, Arkaitz ^a   Elmore, Simon ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Amides; Arylation; Cross coupling; Heterogeneous catalysis; Iron; Sustainable chemistry

Indexed keywords

SULFUR COMPOUNDS;

ARYLATION; CROSS-COUPLING; HETEROGENEOUS CATALYSIS; IRON; SUSTAINABLE CHEMISTRY;

AMIDES;

AMIDE; FERRIC CHLORIDE; FERRIC ION;

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

AMIDES; CATALYSIS; FERRIC COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 44349112602     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800293     Document Type: Article

References (43)

1. For general reviews, see: a) S. V. Ley, A. W. Thomas. Angew. Chem. 2003, 115, 5558;
2. Angew. Chem. Int. Ed. 2003. 42, 5400:
3. b) I. P. Beletskaya. A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337;
4. c) J.-P. Corbert, G. Mignani, Chem. Rev. 2006, 106, 2651:
5. d) J.F. Hartwig, Synlett 2006, 1283.
6. a) J. Yin. S. L. Buchwald. J. Am. Chem. Soc. 2002, 124, 6043:
7. b) X. Huang. K. W. Anderson, D. Zim, L. Jiang, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653;
8. c) T. Ikawa, T. E. Bader, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 13001;
9. d) Q. Shen, J. F. Hartwig. J. Am. Chem. Soc. 2007, 129, 7734.
10. a) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald. J. Am. Chem. Soc. 2001, 123, 7727;
11. b) A. Klapars, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 7421;
12. c) E. R. Strieter, D. G. Blackmond, S. L. Buchwald. J. Am. Chem. Soc. 2005, 127, 4120.
13. For general overviews on iron catalysis, see: a) C Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217;
14. b) A. Fürstner, R. Martin. Chem. Lett. 2005, 624.
15. See, for example: a) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632;
16. Angew. Chem. Int. Ed. 2002, 41, 609;
17. b) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856;
18. c) R. Martin, A. Fürstner. Angew. Chem. 2004, 116, 4045:
19. Angew. Chem. Int. Ed. 2004, 43, 3955;
20. d) B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner. J. Org. Chem. 2004, 69, 3943:
21. e) I. Sapountzis. W. Lin. C. C. Kofink. C. Despotopoulou, P. Knochel, Angew. Chem. 2005, 117, 1682;
22. Angew. Chem. Int. Ed. 2005, 44, 1654:
23. f) I. lovel, K. Mertins, J. Kischel. A. Zapf. M. Beller. Angew. Chem. 2005, 117, 3981;
24. Angew. Chem. Int. Ed. 2005, 44, 3913:
25. g) C. C. Kofink. B. Blank. S. Pagano, N. Götz, P. Knochel, Chem. Commun. 2007, 1954;
26. h) T. Hatakeyama. M. Nakamura. J. Am. Chem. Soc. 2007, 129, 9844;
27. i) G. Cahiez, C. Duplais, A. Moyeux, Org. Lett. 2007, 9, 3253;
28. j) E. Shirakawa. T. Yamagami, T. Kimura, S. Yamaguchi, T. Hayashi. J. Am. Chem. Soc. 2007, 129, 17164:
29. k) A. Guérinot, S. Reymond. J. Cossy. Angew. Chem. 2007, 119, 6641:
30. Angew. Chem. Int. Ed. 2007, 46, 6521;
31. l) C. M. Rao Volla, P. Vogel. Angew. Chem. 2008, 120, 1325:
32. Angew. Chem. Int. Ed. 2008, 47, 1305:
33. m) R. R. Chowdhury, A. K. Crane. C. Fowler, P. Kwong, C. M. Kozak, Chem. Commun. 2008, 94.
34. a) A. Correa, C. Bolm, Angew. Chem. 2007, 119, 9018:
35. Angew. Chem. Int. Ed. 2007, 46, 8862:
36. b) A. Correa. C. Bolm, Adv. Synth. Catal. 2008, 350, 391.
37. O. Bistri, A. Correa, C Bolm, Angew. Chem. 2008, 120, 596:
38. Angew. Chem. Int. Ed. 2008, 47, 586.
39. A. Correa, M. Carril. C. Bolm. Angew. Chem. DOI: 10.1002/ange.200705668;
40. Angew. Chem. Int. Ed. DOI: 10.1002/anie.200705668.
41. Related N-aryl derivatives prepared by copper-catalyzed arylation of o-haloanilides are useful intermediates for the synthesis of important heterocycles. For examples, see: a) C. P. Jones, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2007, 72, 7968;
42. b) N. Zheng, S. L. Buchwald, Org. Lett. 2007, 9, 4749.
43. Couplings of benzamide with 4-bromoanisole and 3-bromonitrobenzene gave the corresponding N-aryl benzamides with 15 and 17% yield, respectively.