Room-temperature copper-catalyzed carbon-nitrogen coupling of aryl iodides and bromides promoted by organic ionic bases

Angewandte Chemie - International Edition

Volumn 48, Issue 40, 2009, Pages 7398-7401

  Yang, Chu Ting ^a   Fu, Yao ^a   Huang, Yao Bing ^a   Yi, Jun ^a   Guo, Qing Xiang ^a   Liu, Lei ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

C N bond formation; Copper; Cross coupling; Ionic bases; Omogeneous catalysis

Indexed keywords

AROMATIC AMINES; ARYL IODIDES; C-N BOND FORMATION; CONDUCTIVITY MEASUREMENTS; CROSS-COUPLING; IONIC BASES; N-HETEROCYCLES; OMOGENEOUS CATALYSIS; PHOSPHONIUM CATIONS; ROOM TEMPERATURE; TETRAALKYLAMMONIUM;

AMINES; BROMINE COMPOUNDS; CATALYSIS; ORGANIC SOLVENTS;

COPPER;

EID: 70349913565     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903158     Document Type: Article

References (56)

1. a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
2. b) R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41,1461;
3. c) J. F. Hartwig, Acc. Chem. Res. 2008, 41,1534;
4. d) M. Kienle, S. R. Dubbaka, K. Brade, P. Knöchel, Eur. J. Org. Chem. 2007, 4166.
5. Previous reports for the use of tetraethylammonium carbonate in Cu-catalyzed N-arylations: L. Liu, M. Frohn, N Xi, C. Dominguez, R. Hungate, P. J. Reider, J. Org. Chem. 2005, 70, 10135.
6. Two organic ionic bases are commercially available: tetraethylammonium carbonate (Fluka) and tetrabutylammonium phosphate monobasic (Sigma-Aldrich).
7. Reviews: a) S. V Ley, A. W Thomas, Angew. Chem. 2003, 115, 5558;
8. Angew. Chem. Int. Ed. 2003, 42, 5400;
9. b) W. Deng, L. Liu, Q.-X. Guo, Chin. J. Org. Chem. 2004, 24,150;
10. c) D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41, 1450;
11. d) F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140;
12. Angew. Chem. Int. Ed. 2008, 47, 3096;
13. e) G. Evano, N Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
14. A. Shafir, S. L. Buchwald, J. Am. Chem. Soc. 2006, 128, 8742.
15. For related studies on Cu-catalyzed couplings under mild conditions, see: a) S. F. Yip, H. Y Cheung, Z. Zhou, F.Y. Kwong, Org. Lett. 2007, 9, 3469;
16. b) A. Ouali, R. Laurent, A.M. Caminade, J.-P. Majorai, M. Taillefer, J. Am. Chem. Soc. 2006, 128, 15990;
17. c) F. Monnier, F. Turtaut, L. Duroure, M. Taillefer, Org. Lett. 2008, 10, 3203;
18. d) D Wang, K. Ding, Chem. Commun. 2009,1891.
19. a) C. M. Starks, Z Am. Chem. Soc. 1971, 93, 195;
20. b) H. Ohno, K. Fukumoto, Acc. Chem. Res. 2007, 40, 1122.
21. Previously the lowest temperature for the successful Cucatalyzed cross-couplings between amines and bromobenzenes was 70-90 °C See : a) H. Zhang, Q. Cai, D. Ma, Org. Lett. 2003, 5, 2453;
22. b) H. Rao, H. Fu, Y, Jiang, Y. Zhao, J. Org. Chem. 2005, 70, 8107.
23. Previously the lowest temperature for the successful Cucatalyzed cross-couplings between anilines and iodobenzenes was about 80-90°C See: a) H. Zhang, Q. Cai, D Ma, J. Org. Chem. 2005, 70, 5164;
24. b) R. A. Altman, K. W Anderson, S. L. Buchwald, J. Org. Chem. 2008, 73, 5167.
25. Previously the lowest temperature for the successful Cucatalyzed coupling of ArI with N-heterocycles was 25-90°C: a) R. A. Altman, E. D. Koval, S. L. Buchwald, J. Org. Chem. 2007, 72, 6190;
26. b) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Chem. Eur. J. 2004, 10, 5607;
27. c) H.-J. Cristau, P. P. Cellier, J.-F. Spindler, M. Taillefer, Eur. J. Org. Chem. 2004, 695;
28. d) X. Lv, W Bao, J. Org. Chem. 2007, 72, 3863.
29. a) I Kim, S. Chang, Chem. Commun. 2008, 3052;
30. b) N. Xia, M. Taillefer, Angew. Chem. 2009,121, 343;
31. Angew. Chem. Int. Ed. 2009, 48, 337;
32. c) N. Xia, M. Taillefer, Fr 06827, 2007 and PCT 051701 2008 >.
33. a) E. R. Strieter, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4120;
34. b) A. Ouali, J.-F. Spindler, A. Jutand, M. Taillefer, Adv. Synth. Catal. 2007, 349,1906;
35. c) S.-L. Zhang, L. Liu, Y. Fu, Q.-X. Guo, Organometallics 2007, 26, 4546;
36. d) A. Ouali, M. Taillefer, J.-F. Spindler, A. Jutand, Organometallics 2007, 26, 65;
37. e) R. A. Altman, E. D Koval, S. L. Buchwald, J. Org. Chem. 2007, 72, 6190;
38. f) R. A. Altman, A. M. Hyde, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 9613;
39. g) L. M. Huffman, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 9196;
40. h) M. Mansopur, R. Giacovazzi, A. Ouali, A. Jutand, M. Taillefer, Chem. Commun. 2008, 6051;
41. i) H. Kaddouri, V. Vicente, A. Ouali, F. Ouazzani, M. Taillefer, Angew. Chem. 2009,121, 339;
42. Angew. Chem. Int. Ed. 2009, 48, 333.
43. J. W Tye, Z. Weng, A. M. Johns, C. D Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 9971.
44. E. R. Strieter, B. Bhayana, S. Buchwald, J. Am. Chem. Soc. 2009, 131, 78.
45. Some examples: a) M. Carril, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 4940;
46. Angew. Chem. Int. Ed. 2008, 47, 4862;
47. b) Q. Shen, T Ogata, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 6586;
48. c) H.-J. Cristau, P. P. Cellier, S. Hamada, J.-F. Spindler, M. Taillefer, Org. Lett. 2004, 6, 931;
49. d) G. Nordmann, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 4978.
50. The correct choice of base has been, and will continue to be, important for the optimization of catalytic as well as noncatalytic organic reactions, see: a) D Tzalis, P. Knöchel, Angew. Chem. 1999, 111, 1547;
51. Angew. Chem. Int. Ed. 1999, 38, 1463;
52. b) A. L. Rodriguez, K. Christopher, D. Wolfgang, P. Knöchel, Angew. Chem. 2000, 112, 2607;
53. Angew. Chem. Int. Ed. 2000, 39, 2488;
54. c) L. M. Alcazar-Roman, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 12905;
55. d) M. Taillefer, N. Rahier, A. Hameau, Chem. Commun. 2006, 3238;
56. e) S. Shekhar, J. F. Hartwig, Organometallics 2007, 26, 340.