An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid

Synlett

Volumn , Issue 13, 2006, Pages 2094-2098

  Li, Lian Hua ^a   Pan, Zhen Liang ^a   Duan, Xin Hua ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Ionic liquid; Microwave; Palladium; Potassium hexacyanoferrate(II)

Indexed keywords

ARYL NITRILE; ARYLVINYL NITRILE; IONIC LIQUID; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYANATION; MICROWAVE RADIATION; SYNTHESIS;

EID: 33748275848     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-947364     Document Type: Article

References (63)

1. (a) Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989, 819.
2. (b) Grundmann, C. In Houben-Weyl: Methoden der organischen Chemie, 4th ed., Vol. E5; Falbe, J., Ed.; Thieme: Stuttgart, 1985, 1313.
3. For the nickel-catalyzed cyanation of aryl halides, see: (a) Cassar, L. J. Organomet. Chem. 1973, 54, 57.
4. (b) Cassar, L.; Foà, M.; Montanari, F.; Marinelli, G. P. J. Organomet. Chem. 1979, 173, 335.
5. (c) Sakakibara, Y.; Okuda, F.; Shimoyabashi, A.; Kirino, K.; Sakai, M.; Uchino, N.; Takagi, K. Bull. Chem. Soc. Jpn. 1988, 61, 1985.
6. (d) Sakakibara, Y.; Ido, Y.; Sasaki, K.; Sakai, M.; Uchino, N. Bull. Chem. Soc. Jpn. 1993, 66, 2776.
7. (e) Rock, M.-H.; Merhold, A. WO 98/37058,1998.
8. For the palladium-catalyzed cyanation of aryl halides, see: (a) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 471.
9. (b) Sekiya, A.; Ishikawa, N. Chem. Lett. 1975, 277.
10. (c) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1975, 48, 3298.
11. (d) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1976, 49, 3177.
12. (e) Dalton, J. R.; Regen, S. L. J. Org. Chem. 1979, 44, 4443.
13. (f) Akita, Y.; Shimazaki, M.; Ohta, A. Synthesis 1981, 974.
14. (g) Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714.
15. (h) Takagi, K.; Sasaki, K.; Sakakibara, Y. Bull. Chem. Soc. Jpn. 1991, 64, 1118.
16. (i) Anderson, Y.; Långström, B. J. Chem. Soc., Perkin Trans. 1 1994, 1395.
17. (j) Okano, T.; Kiji, J.; Toyooka, Y. Chem. Lett. 1998, 425.
18. (k) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224.
19. (l) Maligres, P. E.; Waters, M. S.; Fleitz, F.; Askin, D. Tetrahedron Lett. 1999, 40, 8193.
20. (m) Jin, F.; Confalone, P. N. Tetrahedron Lett. 2000, 41, 3271.
21. Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513.
22. (a) Okano, M.; Amano, M.; Takagi, K. Tetrahedron Lett. 1998, 39, 3001.
23. (b) Ramnauth, J.; Bhardwaj, N.; Renton, P.; Rhakit, S.; Maddafird, S. Synlett 2003, 2237.
24. (c) Tschaen, D. M.; Desmond, R.; King, A. O.; Forin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887.
25. (d) 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.
26. (e) Maligres, P. E.; Waters, M. S.; Fleitz, F.; Askin, D. Tetrahedron Lett. 1999, 40, 8193.
27. (f) Jiang, B.; Kan, Y.; Zhang, A. Tetrahedron 2001, 57, 1581.
28. (a) Chidambaram, R. Tetrahedron Lett. 2004, 45, 1441.
29. (b) Jin, F.; Confalone, P. N. Tetrahedron Lett. 2000, 41, 3271.
30. (c) Okano, T.; Iwahara, M.; Kiji, J. Synlett 1998, 243.
31. (d) Stazi, F.; Palmisano, G.; Turconi, M.; Santagostino, M. Tetrahedron Lett. 2005, 46, 1815.
32. (e) Hatsuda, M.; Seki, M. Tetrahedron Lett. 2005, 46, 1849.
33. (f) Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189.
34. (a) Okano, T.; Kiji, J.; Toyooka, Y. Chem. Lett. 1998, 425.
35. (b) Cassar, L.; Foa, M. J. Organomet. Chem. 1979, 173, 335.
36. (c) Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2003, 42, 1661.
37. (d) Sundermeier, M.; Mutyala, S.; Zapf, A.; Spannenberg, A.; Beller, M. J. Organomet. Chem. 2003, 684, 50.
38. (e) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837.
39. (a) First use of potassium ferrocyanide in this capacity (uncatalyzed reaction): Merz, V.; Weith, W. Ber. Dtsch. Chem. Ges. 1877, 10746.
40. (b) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 12, 1388.
41. (c) Schareina, T.; Zapt, A.; Beller, M. J. Organomet. Chem. 2004, 689, 4576.
42. (d) Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2005, 46, 2585.
43. (e) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508.
44. (a) Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, 2002.
45. (b) Liao, M. C.; Duan, X. H.; Liang, Y. M. Tetrahedron Lett. 2005, 46, 3469.
46. Wu, J. X.; Beck, B.; Ren, R. X. Tetrahedron Lett. 2002, 43, 387.
47. (a) Leadbeater, N. E.; Torenius, H. M.; Tye, H. Tetrahedron 2003, 59, 2253.
48. (b) Cai, L.; Liu, X.; Tao, X.; Shen, D. Synth. Commun. 2004, 34,1215.
49. (c) Srivastava, R. R.; Collibee, S. E. Tetrahedron Lett. 2004, 45, 8895.
50. (d) Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2003, 68, 9122.
51. (e)Arvela, R. K.; Leadbeater, N. E.; Torenius, H. M.; Tye, H. Org. Biomol. Chem. 2003, 1, 1119.
52. (f) Alterman, M.; Hallberg, A. J. Org. Chem. 2000, 65, 7984.
53. 4 was chosen because it was not only most easily manipulated at r.t., but one can be sure to be able to separate the product from the solvent completely via simple extraction with a conventional organic solvent and reused.
54. 2O is ground to a fine powder and dried under vacuum (ca. 2 mbar) at 80 °C overnight.
55. Microwave experiments were conducted using a CEM Discover Synthesis Unit (CEM Corp., Matthews, NC). The machine consists of a continuous focused microwave power delivery system with operator selectable power output from 0-300 W.
56. For recent examples, see: (a) Ho, T.-L.; Su, C.-Y. J. Org. Chem. 2000, 65, 3566.
57. (b) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B. J. Am. Chem. Soc. 1999, 121, 4900.
58. (c) Carless, H. A. J.; Dove, Y. Tetrahedron: Asymmetry 1996, 7, 649.
59. (a) Fleming, F. F.; Pu, Y.; Tercek, F. J. Org. Chem. 1997, 62, 4883.
60. (b) Fleming, F. F.; Hussain, Z.; Weaver, D.; Norman, R. E. J. Org. Chem. 1997, 62, 1305.
61. (c) Fleming, F. F.; Pak, J. J. J. Org. Chem. 1995, 60, 4299.
62. 2 (2.5 mol%), and DMEDA (10 mol%). After sealing the tube, the mixture was exposed to microwave irradiation (a maximum microwave power of 120 W, a temperature threshold of 200 °C and a pressure threshold of 200 psi) for the requisite time. After the reaction mixture was cooled, the product was extracted from the system by washing the ionic liquid repeatedly with EtOAc-PE = 8:1 (4 × 3 mL). Finally, the product was isolated by flash chromatography on silica gel using EtOAc-PE as mobile phase.
63. +], 152, 76.