Mild and highly efficient metal-free oxidative α-cyanation of N-acyl/sulfonyl tetrahydroisoquinolines

RSC Advances

Volumn 4, Issue 104, 2014, Pages 60075-60078

  Yan, Changcun ^a   Liu, Yuxiu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYANATION; CYANATION REACTION; CYANO GROUPS; FLUOROBORATE SALTS; TETRAHYDROISOQUINOLINES; TRIMETHYLSILYL CYANIDE;

EID: 84912006364     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra12922a     Document Type: Article

References (59)

1. (a) C.-J. Li, Acc. Chem. Res., 2009, 42, 335;
2. (b) J. A. Ashenhurst, Chem. Soc. Rev., 2010, 39, 540;
3. (c) C. L. Li, B. J. Sun and Z. J. Shi, Chem. Rev., 2011, 111, 1293;
4. (d) C. S. Yeung and V. M. Dong, Chem. Rev., 2011, 111, 1215;
5. (e) S. H. Cho, J. Y. Kim, J. Kwak and S. Chang, Chem. Soc. Rev., 2011, 40, 5068;
6. (f) C. Liu, H. Zhang, W. Shi and A. W. Lei, Chem. Rev., 2011, 111, 1780;
7. (g) C. Zhang, C. H. Tang and N. Jiao, Chem. Soc. Rev., 2012, 41, 3464;
8. (h) X. Shang and Z. Q. Liu, Chem. Soc. Rev., 2013, 42, 3253;
9. (i) S. A. Girard, T. Knauber and C.-J. Li, Angew. Chem., Int. Ed., 2014, 53, 74.
10. (a) M. Shamma and J. T. Moniot, The Isoquinoline Alkaloids, Chemistry and Pharmacology, Academic Press, New York and London, 1972;
11. (b) R. B. Herbert, The Chemistry and Biology of Isoquinoline Alkaloids, Springer Verlag, Berlin, Heidelberg, New York, Tokyo, 1985, p. 213;
12. (c) D. Jack and R. Williams, Chem. Rev., 2002, 102, 1669;
13. (d) F. Louafi, J.-P. Hurvois, A. Chibani and T. Roisnel, J. Org. Chem., 2010, 75, 5721;
14. (e) F. Louafi, J. Moreau, S. Shahane, S. Golhen, T. Roisnel, S. Sinbandhit and J.-P. Hurvois, J. Org. Chem., 2011, 76, 9720.
15. M. North, Angew. Chem., Int. Ed., 2004, 43, 4126.
16. (a) S.-I. Murahashi, N. Komiya, H. Terai and T. Nakae, J. Am. Chem. Soc., 2003, 125, 15312;
17. (b) S.-I. Murahashi, N. Komiya and H. Terai, Angew. Chem., Int. Ed., 2005, 44, 6931;
18. (c) S.-I. Murahashi, T. Nakae, H. Terai and N. Komiya, J. Am. Chem. Soc., 2008, 130, 11005;
19. (d) S. Singhal, S. L. Jain and B. Sain, Chem. Commun., 2009, 2371;
20. (e) W. Han and A. R. Ofial, Chem. Commun., 2009, 5024;
21. (f) S. Singhal, S. L. Jain and B. Sain, Adv. Synth. Catal., 2010, 352, 1338;
22. (g) J. M. Allen and T. H. Lambert, J. Am. Chem. Soc., 2011, 133, 1260;
23. (h) S. Verma, S. L. Jain and B. Sain, ChemCatChem, 2011, 3, 1329;
24. (i) S. Verma, S. L. Jain and B. Sain, Catal. Lett., 2011, 141, 882;
25. (j) Y. Zhang, H. Peng, M. Zhang, Y. X. Cheng and C. J. Zhu, Chem. Commun., 2011, 47, 2354;
26. (k) M. Rueping, S. Q. Zhu and R. M. Koenigs, Chem. Commun., 2011, 47, 12709;
27. (l) Y. H. Pan, S. Wang, C. W. Kee, E. Dubuisson, Y. Y. Yang, K. P. Loh and C. H. Tan, Green Chem., 2011, 13, 3341;
28. (m) K. Alagiri and K. R. Prabhu, Org. Biomol. Chem., 2012, 10, 835;
29. (n) W. P. To, G. S. M. Tong, W. Lu, C. Ma, J. Liu, A. L. F. Che and C. M. Chow, Angew. Chem., Int. Ed., 2012, 51, 2654;
30. (o) K. T. V. Rao, B. Haribadu, P. S. S. Prasad and N. Lingaiah, ChemCatChem, 2012, 4, 1173;
31. (p) M. Rueping, J. Zoller, D. C. Fabry, K. Poscharny, R. M. Koenigs, T. E. Weirich and J. Mayer, Chem.-Eur. J., 2012, 18, 3478;
32. (q) D. B. Freeman, L. Furst, A. G. Condie and C. R. Stephenson, Org. Lett., 2012, 14, 94;
33. (r) L. H. Liu, Z. K. Wang, X. F. Fu and C. H. Yan, Org. Lett., 2012, 14, 5692;
34. (s) N. Sakai, A. Mutsuro, R. Ikeda and T. Konakahra, Synlett, 2013, 24, 1283;
35. (t) G. Zhang, Y. X. Ma, G. B. Cheng, D. B. Liu and R. Wang, Org. Lett., 2014, 16, 656;
36. (u) H. Ueda, K. Yoshida and H. Tokuyama, Org. Lett., 2014, 16, 4194.
37. (a) H. Richter and O. G. Mancheno, Eur. J. Org. Chem., 2010, 4460;
38. (b) M. Ghobrial, K. Harhammer, M. D. Mihovilovic and M. Schnurch, Chem. Commun., 2010, 46, 8836;
39. (c) M. Ghobrial, M. Schnurch and M. D. Mihovilovic, J. Org. Chem., 2011, 76, 8781;
40. (d) H. Richter, R. Frohlich, C.-G. Daniliuc and O. G. Mancheno, Angew. Chem., Int. Ed., 2012, 51, 8656;
41. (e) B. Schweitzer-Chaput and M. Klussmann, Eur. J. Org. Chem., 2013, 666;
42. (f) X. G. Liu, B. Sun, Z. Y. Xie, X. J. Qin, L. Liu and H. X. Lou, J. Org. Chem., 2013, 78, 3104;
43. (g) Z. Y. Xie, L. Liu, W. F. Chen, H. B. Zheng, Q. Q. Xu, H. Q. Yuan and H. X. Lou, Angew. Chem., Int. Ed., 2014, 53, 3904.
44. S. S. Libendi, Y. Demizu and O. Onomura, Org. Biomol. Chem., 2009, 7, 351.
45. S. Kamijo, T. Hoshikawa and M. Inoue, Org. Lett., 2011, 13, 5928.
46. (a) W. F. Bailey, J. M. Bobbitt and K. B. Wiberg, J. Org. Chem., 2007, 72, 4504;
47. (b) C. X. Miao, L. N. He, J. Q. Wang and J. L. Wang, Adv. Synth. Catal., 2009, 351, 2209.
48. TEMPO was detected and was isolated from the reaction system.
49. M. F. Semmelhack, C. R. Schmid, D. A. Cortes and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374.
50. (a) D. J. Newman and G. M. Cragg, J. Nat. Prod., 2004, 67, 1216;
51. (b) M. Sasaki and H. Fuwa, Synlett, 2004, 1851;
52. (c) I. Kadota and Y. Yamamoto, Acc. Chem. Res., 2005, 38, 423.
53. (d) Y. H. Zhang and C.-J. Li, Angew. Chem., Int. Ed., 2006, 45, 1949;
54. (e) Y. H. Zhang and C.-J. Li, J. Am. Chem. Soc., 2006, 128, 4242;
55. (f) P. Maity, H. D. Srinivas and M. P. Waston, J. Am. Chem. Soc., 2011, 133, 17142;
56. (g) H. Richter, R. Rohlmann and O. G. Mancheno, Chem.-Eur. J., 2011, 17, 11622;
57. (h) S. J. Park, J. R. Price and M. H. Todd, J. Org. Chem., 2012, 77, 949;
58. (i) W. Muramatsu, K. Nakano and C.-J. Li, Org. Lett., 2013, 15, 3650.
59. When 1.5 equiv. of TEMPO was added, 2a was obtained in 91% yield, which is essentially the same as the 94% yield obtained when TEMPO was not added.