L-proline-promoted Rosenmund-von Braun reaction

Synlett

Volumn , Issue 1, 2008, Pages 0069-0072

  Wang, Deping ^a   Kuang, Liping ^a,b   Li, Zhengwei ^a   Ding, Ke ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Aryl halides; Aryl nitriles; Copper; L proline; Rosenmund von Braun reaction

Indexed keywords

BROMIDE; FUNCTIONAL GROUP; NITRILE; PROLINE;

ARTICLE; CHEMICAL REACTION; CYANATION; LOW TEMPERATURE; ROSENMUND VON BRAUN REACTION; SYNTHESIS;

EID: 38549150228     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992409     Document Type: Article

References (60)

1. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed.; Georg Thieme: Stuttgart, 2001.
2. Larock, R. C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations; VCH: New York, 1989.
3. (a) Hagedorn, F.; Gelbke, H. P. In Ullmanns Enzyklopädie der Technischen Chemie, 4th ed., Vol. 17; Bartholomé, E.; Biekert, E.; Hellmann, H.; Ley, H.; Weigert, W. M.; Weise, E., Eds.; Verlag Chemie: Weinheim, 1979, 333-338.
4. (b) Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779.
5. (c) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
6. (d) Subramanian, L. R. Science of Synthesis, Vol. 19; Georg Thieme: Stuttgart, 2004, 163.
7. (a) Rosenmund, K. W.; Struck, E. Ber. Dtsch. Chem. Ges. 1919, 2, 1749.
8. (b) Mowry, D. F. Chem. Rev. 1948, 42, 189.
9. (c) Friedrich, K.; Wallenfels, K. In The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Interscience: London, 1970, 67.
10. (d) Lindley, J. Tetrahedron 1984, 40, 1433.
11. (e) Kurtz, P. In Houben-Weyl, Methoden der Organischen Chemie, 4th ed., Part III, Vol. 8; Müller, E., Ed.; Georg Thieme: Stuttgart, 1952, 302.
12. For the palladium-catalyzed cyanation of aryl halides, see: (a) Takagi, K. Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; John Wiley and Sons, Inc.: New York, 2002, 657-672.
13. (b) Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem. Eur. J. 2003, 9, 1828; and the references therein.
14. (c) Polshettiwar, V.; Hesemann, P.; Moreau, J. J. E. Tetrahedron 2007, 63, 6784.
15. (d) Dolakova, P.; Masojidkova, M.; Holy, A. Heterocycles 2007, 71, 1107.
16. (e) Cheng, Y.; Duan, Z.; Li, T.; Wu, Y. Synlett 2007, 543.
17. (f) Littke, A.; Soumeillant, M.; Kaltenbach, R. F. III; Cherney, R. J.; Tarby, C. M.; Kiau, S. Org. Lett. 2007, 9, 1711.
18. (g) Schareina, T.; Zapf, A.; Maegerlein, W.; Mueller, N.; Beller, M. Tetrahedron Lett. 2007, 48, 1087.
19. (h) Dobbs, K. D.; Marshall, W. J.; Grushin, V. V. J. Am. Chem. Soc. 2007, 129, 30.
20. (i) Zhang, Z.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331.
21. (j) Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189.
22. (k) Chobanian, H. R.; Fors, B. P.; Lin, L. S. Tetrahedron Lett. 2006, 47, 3303.
23. (l) Jensen, R. S.; Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Tetrahedron Lett. 2005, 46, 8645.
24. (m) Veauthier, J. M.; Carlson, C. N.; Collis, G. E.; Kiplinger, J. L.; John, K. D. Synthesis 2005, 2683.
25. (n) Hatsuda, M.; Seki, M. Tetrahedron 2005, 61, 9908.
26. (o) Takanami, T.; Hayashi, M.; Chijimatsu, H.-i.; Inoue, W.; Suda, K. Org. Lett. 2005, 7, 3937.
27. (p) Hatsuda, M.; Seki, M. Tetrahedron Lett. 2005, 46, 1849.
28. (q) Stazi, F.; Palmisano, G.; Turconi, M.; Santagostino, M. Tetrahedron Lett. 2005, 46, 1815.
29. (r) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508.
30. (s) Marcantonio, K. M.; Frey, L. F.; Liu, Y.; Chen, Y.; Strine, J.; Phenix, B.; Wallace, D. J.; Chen, C.-Y. Org. Lett. 2004, 6, 3723.
31. (t) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837.
32. (u) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 12, 1388.
33. (v) Chidambaram, R. Tetrahedron Lett. 2004, 45, 1441.
34. (w) Erker, T.; Nemec, S. Synthesis 2004, 23.
35. (x) Ramnauth, J.; Bhardwaj, N.; Renton, P.; Rakhit, S.; Maddaford, S. P. Synlett 2003, 2237.
36. (y) Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2003, 42, 1661.
37. For the nickel-catalyzed cyanation of aryl halides, see: (a) Cassar, L.; Foà, M.; Montanari, F.; Marinelli, G. P. J. Organomet. Chem. 1979, 173, 335.
38. (b) Sakakibara, Y.; Okuda, F.; Shimoyabashi, A.; Kirino, K.; Sakai, M.; Uchino, N.; Takagi, K. Bull. Chem. Soc. Jpn. 1988, 61, 1985.
39. (c) Sakakibara, Y.; Ido, Y.; Sasaki, K.; Sakai, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776.
40. (d) Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2003, 68, 9122.
41. (a) Cristau, H. J.; Ouali, A.; Spindler, J. F.; Taillefer, M. Chem. Eur. J. 2005, 11, 2483.
42. (b) Zanon, J.; Klapers, A.; Buchald, S. L. J. Am. Chem. Soc. 2003, 126, 2890.
43. (c) Wu, J. X.; Beck, B.; Ren, R. X. Tetrahedron Lett. 2002, 43, 387.
44. (d) Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2005, 46, 2585.
45. (a) Guo, X.; Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2006, 348, 2197.
46. (b) Ma, D.; Liu, F. Chem. Commun. 2004, 1934.
47. (c) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
48. (d)Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
49. (e) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
50. (f) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
51. (g) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
52. (h) Deng, W.; Zou, Y.; Wang, Y. F.; Liu, L.; Guo, Q. X. Synlett 2004, 1254.
53. (i) Deng, W.; Zhang, Ch.; Liu, M.; Zou, Y.; Liu, L.; Guo, Q. X. Chin. J. Chem. 2005, 23, 1241.
54. (j) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
55. (a) Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
56. (b) Zhu, W.; Ma, D. J. Org. Chem. 2005, 70, 2696.
57. (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
58. (d) Xie, X.; Cai, G. R.; Ma, D. Org. Lett. 2005, 7, 4693.
59. (e) Lu, B.; Ma, D. Org. Lett. 2006, 8, 6115.
60. 3): δ = 3.99 (3 H, s), 6.80 (1 H, d, J = 8.4 Hz), 7.76 (1 H, dd, J = 2.0, 8.4 Hz), 8.48 (1 H, s).