Metal-free intramolecular carbocyanation of activated alkenes: Functionalized nitriles bearing β-quaternary carbon centers

Angewandte Chemie - International Edition

Volumn 52, Issue 35, 2013, Pages 9296-9300

  Chen, Jianming ^a   Zou, Gongfeng ^a   Liao, Weiwei ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

asymmetric synthesis; heterocycles; homogeneous catalysis; nitriles; synthetic methods

Indexed keywords

ASYMMETRIC SYNTHESIS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; NITRILES; SYNTHETIC METHODS;

CARBON; HYDROCARBONS; REACTION KINETICS;

CYANIDES;

ALKENE; CARBON; NITRILE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; HETEROCYCLES; HOMOGENEOUS CATALYSIS; SYNTHESIS; SYNTHETIC METHODS;

ASYMMETRIC SYNTHESIS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; NITRILES; SYNTHETIC METHODS;

ALKENES; CARBON; MOLECULAR STRUCTURE; NITRILES;

EID: 84882974262     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304102     Document Type: Article

References (60)

1. A. J. Fatiadi, in Preparation and Synthetic Applications of Cyano Compounds (Eds.:, S. Patai, Z. Rappaport,), Wiley, New York, 1983
2. R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989.
3. "Three Carbon-Heteroatom Bonds: Nitriles, Isocyanides, and Dervatives": Science of Synthesis, Vol.19 (Ed.:, S. Murahashi,), Georg Thieme, Stuttgart, 2004.
4. Y. Nakao, T. Hiyama, Pure Appl. Chem. 2008, 80, 1097
5. M. Tobisu, N. Chatani, Chem. Soc. Rev. 2008, 37, 300
6. C. Nájera, J. Sansano, Angew. Chem. 2009, 121, 2488
7. Angew. Chem. Int. Ed. 2009, 48, 2452
8. S. M. Bonesi, M. Fagnoni, Chem. Eur. J. 2010, 16, 13572
9. M. Murakami, T. Matsuda, Chem. Commun. 2011, 47, 1100
10. G. P. Wolfe, Angew. Chem. 2012, 124, 10370
11. Angew. Chem. Int. Ed. 2012, 51, 10224
12. Y. Nakao, Bull. Chem. Soc. Jpn. 2012, 85, 731; for selected recent examples for other cyanofunctionalizations, see
13. S. Arai, T. Sato, Y. Koike, M. Hayashi, A. Nishida, Angew. Chem. 2009, 121, 4598
14. Angew. Chem. Int. Ed. 2009, 48, 4528
15. M. Suginome, A. Yamamoto, M. Murakami, Angew. Chem. 2005, 117, 2432
16. Angew. Chem. Int. Ed. 2005, 44, 2380
17. I. Kamiya, J. Kawakami, S. Yano, A. Nomoto, A. Ogawa, Organometallics 2006, 25, 3562
18. M. Murai, R. Hatano, S. Kitabata, K. Ohe, Chem. Commun. 2011, 47, 2375
19. D. C. Koester, M. Kobayashi, D. B. Werz, Y. Nakao, J. Am. Chem. Soc. 2012, 134, 6544.
20. Y. Yasui, H. Kamisaki, Y. Takemoto, Org. Lett. 2008, 10, 3303
21. Y. Yasui, H. Kamisaki, T. Ishida, Y. Takemoto, Tetrahedron 2010, 66, 1980
22. Y. Kobayashi, H. Kamisaki, R. Yanada, Y. Takemoto, Org. Lett. 2006, 8, 2711
23. Y. Kobayashi, H. Kamisaki, H. Takeda, Y. Yasui, R. Yanada, Y. Takemoto, Tetrahedron 2007, 63, 2978
24. M. P. Watson, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 12594
25. Y. Nakao, S. Ebata, A. Yada, T. Hiyama, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2008, 130, 12874
26. Y. Yasui, T. Kinugawa, Y. Takemoto, Chem. Commun. 2009, 4275.
27. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363
28. B. M. Trost, C. Jiang, Synthesis 2006, 369
29. M. Bella, T. Gasperi, Synthesis 2009, 1583
30. C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295
31. J. P. Das, I. Marek, Chem. Commun. 2011, 47, 4593.
32. D. Berthiaume, D. Poirier, Tetrahedron 2000, 56, 5995
33. S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195
34. A. Baeza, C. Najera, M. G. Retamosa, J. M. Sansano, Synthesis 2005, 2787
35. S. K. Tian, L. Deng, Tetrahedron 2006, 62, 11320
36. D. Peng, H. Zhou, X.-H. Liu, L.-W. Wang, S.-K. Chen, X.-M. Feng, Synlett 2007, 2448
37. S. Matsukawa, I. Sekine, A. Iitsuka, Molecules 2009, 14, 3353; for examples of Lewis base catalyzed the acylcyanation of imines, see
38. S. C. Pan, J. Zhou, B. List, Synlett 2006, 3275
39. S. C. Pan, B. List, Synlett 2007, 318
40. S. C. Pan, J. Zhou, B. List, Angew. Chem. 2007, 119, 618
41. Angew. Chem. Int. Ed. 2007, 46, 612
42. S. C. Pan, B. List, Org. Lett. 2007, 9, 1149.
43. Z. Zhuang, J.-M. Chen, F. Pan, W.-W. Liao, Org. Lett. 2012, 14, 2354
44. Z. Zhuang, F. Pan, J.-G. Fu, J.-M. Chen, W.-W. Liao, Org. Lett. 2011, 13, 6164
45. T.-Y. Qin, W.-W. Liao, Y.-J. Zhang, S. X.-A. Zhang, Org. Biomol. Chem. 2013, 11, 984
46. F. Pan, J.-M. Chen, Z. Zhuang, Y.-Z. Fang, S. X.-A. Zhang, W.-W. Liao, Org. Biomol. Chem. 2012, 10, 2214.
47. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535
48. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035
49. L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37, 1140
50. B. J. Cowen, S. J. Miller, Chem. Soc. Rev. 2009, 38, 3102
51. A. Marinetti, A. Voituriez, Synlett 2010, 174.
52. M. North, M. Omedes-Pujol, C. Young, Org. Biomol. Chem. 2012, 10, 4289
53. M. Ohashi, H. Maeda, K. Mizuno, Chem. Lett. 2010, 39, 462
54. P. Areces, E. Carrasco, M. E. Light, J. Plumet, Synlett 2009, 2500
55. A. Aljarilla, R. Cordoba, A. G. Csaky, I. Fernandez, F. L. Ortiz, J. Plumet, G. RuizGomez, Eur. J. Org. Chem. 2006, 3969
56. B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Org. Lett. 2005, 7, 3981
57. B. T. Holmes, A. W. Snow, Tetrahedron 2005, 61, 12339
58. I. Amurrio, R. Cordoba, A. G. Csaky, J. Plumet, Tetrahedron 2004, 60, 10521
59. R. Vidya, M. Eggen, S. K. Nair, G. I. Georg, R. H. Himes, J. Org. Chem. 2003, 68, 9687.
60. H. W. Gibson, M. A. G. Berg, J. CliftonDickson, P. R. Lecavalier, H. Wang, J. S. Merola, J. Org. Chem. 2007, 72, 5759.