Catalytic cyanation of aryl iodides using DMF and ammonium bicarbonate as the combined source of cyanide: A dual role of copper catalysts

Chemical Communications

Volumn 50, Issue 4, 2014, Pages 448-450

  Pawar, Amit B ^a,b   Chang, Sukbok ^a,b  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; AMMONIUM BICARBONATE; ARYL IODIDE DERIVATIVE; BICARBONATE; COPPER; CYANIDE; IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYANATION; ELECTRON;

EID: 84889776908     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc47926a     Document Type: Article

References (61)

1. The Chemistry of the Cyano Group, ed. Z. Rappoport, Interscience, London, 1970
2. R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, VCH, New York, 1989
3. A. Kleemann, J. Engel, B. Kutscher and D. Reichert, Pharmaceutical Substance: Synthesis, Patents, Applications, 4th edn, Georg Thieme, Stuttgart, 2001
4. J. S. Miller, J. L. Manson, Acc. Chem. Res. 2001, 34, 563
5. F. F. Fleming, Q. Wang, Chem. Rev. 2003, 103, 2035
6. T. Sandmeyer, Ber. Dtsch. Chem. Ges. 1884, 17, 1633
7. C. Galli, Chem. Rev. 1988, 88, 765
8. K. W. Rosenmund, E. Struck, Ber. Dtsch. Chem. Ges. 1919, 2, 1749
9. J. Lindley, Tetrahedron 1984, 40, 1433
10. G. P. Ellis, T. M. Romney-Alexander, Chem. Rev. 1987, 87, 779
11. P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 2011, 40, 5049
12. T. Okano, M. Iwahara, J. Kiji, Synlett 1998, 243
13. J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890
14. C. Yang, J. M. Williams, Org. Lett. 2004, 6, 2837
15. H.-J. Cristau, A. Ouali, J.-F. Spindler, M. Taillefer, Chem.–Eur. J. 2005, 11, 2483
16. P. E. Maligres, M. S. Waters, F. Fleitz, D. Askin, Tetrahedron Lett. 1999, 40, 8193
17. M. Alterman, A. Hallberg, J. Org. Chem. 2000, 65, 7984
18. F. G. Buono, R. Chidambaram, R. H. Mueller, R. E. Waltermire, Org. Lett. 2008, 10, 5325
19. T. Schareina, A. Zapf, M. Beller, Chem. Commun. 2004, 1388
20. S. A. Weissman, D. Zewge, C. Chen, J. Org. Chem. 2005, 70, 1508
21. T. Schareina, A. Zapf, W. Mägerlein, N. Müller, M. Beller, Tetrahedron Lett. 2007, 48, 1087
22. P. Y. Yeung, C. M. So, C. P. Lau, F. Y. Kwong, Angew. Chem. Int. Ed. 2010, 49, 8918
23. P. Y. Yeung, C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett. 2011, 13, 648
24. P. Y. Yeung, C. P. Tsang, F. Y. Kwong, Tetrahedron Lett. 2011, 52, 7038
25. J. Kim, H. J. Kim, S. Chang, Angew. Chem. Int. Ed. 2012, 51, 11948
26. M. Sundermeier, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2003, 42, 1661
27. T. Schareina, A. Zapf, A. Cotté, M. Gotta, M. Beller, Adv. Synth. Catal. 2011, 353, 777
28. E. J. Park, S. Lee, S. Chang, J. Org. Chem. 2010, 75, 2760
29. N. Chatani, T. Hanafusa, J. Org. Chem. 1986, 51, 4714
30. M. Sundermeier, S. Mutyala, A. Zapf, A. Spannenberg, M. Beller, J. Organomet. Chem. 2003, 684, 50
31. R.-J. Song, J.-C. Wu, Y. Liu, G.-B. Deng, C.-Y. Wu, W.-T. Wie, J.-H. Li, Synlett 2012, 2491
32. C. Pan, H. Jin, P. Xu, X. Liu, Y. Cheng, C. Zhu, J. Org. Chem. 2013, 78, 9494
33. Z. Jiang, Q. Huang, S. Chen, L. Long, X. Zhou, Adv. Synth. Catal. 2012, 354, 589
34. J. Jin, Q. Wen, P. Lu, Y. Wang, Chem. Commun. 2012, 48, 9933
35. Y. Luo, Q. Wen, Z. Wu, J. Jin, P. Lu, Y. Wang, Tetrahedron 2013, 69, 8400
36. O. Y. Yuen, P. Y. Choy, W. K. Chow, W. T. Wong, F. Y. Kwong, J. Org. Chem. 2013, 78, 3374
37. Z. Zhang, L. S. Liebeskind, Org. Lett. 2006, 8, 4331
38. G.-Y. Zhang, J.-T. Yu, M.-L. Hu, J. Cheng, J. Org. Chem. 2013, 78, 2710
39. N. Sato, Q. Yue, Tetrahedron 2003, 59, 5831
40. G. Zhang, S. Chen, H. Fei, J. Cheng, F. Chen, Synlett 2012, 2247
41. K. Zheng, P. Yu, S. Chen, F. Chen, J. Cheng, Chin. J. Chem. 2013, 31, 449
42. H. Xu, P.-T. Liu, Y.-H. Li, F.-S. Han, Org. Lett. 2013, 15, 3354
43. S. Zheng, C. Yu, Z. Shen, Org. Lett. 2012, 14, 3644
44. S. Xu, X. Huang, X. Hong, B. Xu, Org. Lett. 2012, 14, 4614
45. J. Peng, J. Zhao, Z. Hu, D. Liang, J. Huang, Q. Zhu, Org. Lett. 2012, 14, 4966
46. G. Kaupp, J. Schmeyers, J. Boy, Chem.–Eur. J. 1998, 4, 2467
47. K. Okamoto, M. Watanabe, M. Murai, R. Hatano, K. Ohe, Chem. Commun. 2012, 48, 3127
48. P. Anbarasan, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 519
49. P. Anbarasan, H. Neumann, M. Beller, Chem.–Eur. J. 2011, 17, 4217
50. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
51. J. Kim, S. Chang, J. Am. Chem. Soc. 2010, 132, 10272
52. J. Kim, J. Choi, K. Shin, S. Chang, J. Am. Chem. Soc. 2012, 134, 2528
53. J. Kim, H. Kim, S. Chang, Org. Lett. 2012, 14, 3924
54. Z. Wang, S. Chang, Org. Lett. 2013, 15, 1990
55. S. Ding, N. Jiao, J. Am. Chem. Soc. 2011, 133, 12374
56. D. N. Sawant, Y. S. Wagh, P. J. Tambade, K. D. Bhatte, B. M. Bhanage, Adv. Synth. Catal. 2011, 353, 781
57. X. Ren, J. Chen, F. Chen, J. Cheng, Chem. Commun. 2011, 47, 6725
58. G. Zhang, X. Ren, J. Chen, M. Hu, J. Cheng, Org. Lett. 2011, 13, 5004
59. K. Zheng, B. Liu, S. Chen, F. Chen, Tetrahedron Lett. 2013, 54, 5250
60. S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400
61. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068