An efficient transformation from benzyl or allyl halides to aryl and alkenyl nitriles

Organic Letters

Volumn 12, Issue 12, 2010, Pages 2888-2891

  Zhou, Wang ^a   Xu, Jiaojiao ^a   Zhang, Liangren ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HALOGENATED HYDROCARBON; NITRILE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; NITRILES;

EID: 77953606644     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101094u     Document Type: Article

References (85)

1. Fatiadi, A. J. In Preparation and Synthetic Applications of Cyano Compounds; Patai, S., Rappaport, Z., Ed.; Wiley: New York, 1983.
2. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989.
3. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substance: Synthesis, Patents, Applications, 4th ed.; Georg Thieme: Stuttgart, 2001.
4. Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34, 563
5. Smith, M. B.; March, J. Marchs Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.; Wiley: Hoboken, NJ, 2007.
6. Fleming, F. F.; Wang, Q. Chem. Rev. 2003, 103, 2035
7. Magnus, P.; Scott, D. A.; Fielding, M. R. Tetrahedron Lett. 2001, 42, 4127
8. Murdoch, D.; Keam, S. J. Drugs 2005, 65, 2379
9. Njar, V. C. O.; Brodie, A. M. H. Drugs 1999, 58, 233
10. Synthesis of nitriles by Sandmeyer and transition-metal-mediated cyanation. For reviews, see
11. Ellis, G. A.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779
12. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047
13. Galli, C. Chem. Rev. 1988, 88, 765
14. For some recent examples, see
15. Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388
16. Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837
17. Chen, G.; Weng, J.; Zheng, Z.; Zhu, X.; Cai, Y.; Cai, J.; Wan, Y. Eur. J. Org. Chem. 2008, 3524
18. Schareina, T.; Zapf, A.; Maegerlein, W.; Müeller, N.; Beller, M. Chem.-Eur. J. 2007, 13, 6249
19. Zhu, Y.-Z.; Cai, C. Eur. J. Org. Chem. 2007, 2401
20. Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189
21. Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem.-Eur. J. 2003, 9, 1828
22. Ren, Y.; Wang, W.; Zhao, S.; Tian, X.; Wang, J.; Yin, W.; Cheng, L. Tetrahedron Lett. 2009, 50, 4595
23. Alterman, M.; Hallberg, A. J. Org. Chem. 2000, 65, 7984
24. Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890
25. Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2005, 11, 2483
26. Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2003, 42, 1661
27. Recent examples for synthesis of nitriles from amides or oximes
28. Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983
29. Kuo, C.-W.; Zhu, J.-L.; Wu, J.-D.; Chu, C.-M.; Yao, C.-F.; Shia, K.-S. Chem. Commun. 2007, 301
30. Choi, E.; Lee, C.; Na, Y.; Chang, S. Org. Lett. 2002, 4, 2369
31. Yamaguchi, K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N. Angew. Chem., Int. Ed. 2007, 46, 3922
32. Zhou, S.; Addis, D.; Das, S.; Junge, K.; Beller, M. Chem. Commun. 2009, 4883
33. Yadav, L. D. S.; Srivastava, V. P.; Patel, R. Tetrahedron Lett. 2009, 50, 5532
34. Singh, M. K.; Lakshman, M. K. J. Org. Chem. 2009, 74, 3079
35. Saha, D.; Saha, A.; Ranu, B. C. Tetrahedron Lett. 2009, 50, 6088
36. Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Org. Lett. 2009, 11, 2461
37. Recent examples for synthesis of nitriles from amines or alcohols
38. Iida, S.; Togo, H. Tetrahedron 2007, 63, 8274
39. Oischi, T.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2009, 48, 6286
40. Chen, F.-E.; Kuang, Y.-Y.; Dai, H.-F.; Lu, L.; Huo, M. Synthesis 2003, 17, 2629
41. Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Prashanthi, S.; Kantam, M. L. Tetrahedron Lett. 2009, 50, 2050
42. Chen, F.-E.; Li, Y.-Y.; Xu, M.; Jia, H.-Q. Synthesis 2002, 13, 1804
43. McAllister, G. D.; Wilfred, C. D.; Taylor, R. J. K. Synlett 2002, 8, 1291
44. Recent examples for direct cyanation through C-H bond functionalization
45. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
46. Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372
47. Dohi, T.; Morimoto, K.; Kiyono, Y.; Tohma, H.; Kita, Y. Org. Lett. 2005, 7, 537
48. Yan, G.; Kuang, C.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 1052
49. Jia, X.; Yang, D.; Zhang, S.; Cheng, J. Org. Lett. 2009, 11, 4716
50. Dohi, T.; Morimoto, K.; Takenaga, N.; Goto, A.; Maruyama, A.; Kiyono, Y.; Tohma, H.; Kita, Y. J. Org. Chem. 2007, 72, 109
51. Jia, X.; Yang, D.; Wang, W.; Luo, F.; Cheng, J. J. Org. Chem. 2009, 74, 9470
52. Lu, Z.; Hu, C.; Guo, J.; Li, J.; Cui, Y.; Jia, Y. Org. Lett. 2010, 12, 480
53. Do, H.-Q.; Daugulis, O. Org. Lett. 2010, 12, 2517
54. Other methods
55. Lücke, B.; Narayana, K. V.; Martin, A.; Jähnisch, K. Adv. Synth. Catal. 2004, 346, 1407
56. Telvekar, V. N.; Patel, K. N.; Kundaikar, H. S.; Chaudhari, H. K. Tetrahedron Lett. 2008, 49, 2213
57. Arote, N. D.; Bhalerao, D. S.; Akamanchi, K. G. Tetrahedron Lett. 2007, 48, 3651
58. Sasson, R.; Rozen, S. Org. Lett. 2005, 7, 2177
59. Rudler, H.; Denis, B. Chem. Commun. 1998, 2145
60. Altamura, A.; Daccolti, L.; Detomaso, A.; Dinoi, A.; Fiorentino, M.; Fusco, C.; Curci, R. Tetrahedron Lett. 1998, 39, 2009
61. Fernandez, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M.; Vazquez, J. Tetrahedron Lett. 1993, 34, 141
62. Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904
63. Nakao, Y.; Yukawa, T.; Hirata, Y.; Oda, S.; Satoh, J.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7116
64. Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428
65. Kojima, S.; Fukuzaki, T.; Yamakawa, A.; Murai, Y. Org. Lett. 2004, 6, 3917
66. Peppe, C.; Mello, P. A.; dasChagas, R. P. J. Organomet. Chem. 2006, 691, 2335
67. Tomioka, T.; Takahashi, Y.; Vaughan, T. G.; Yanase, T. Org. Lett. 2010, 12, 2171
68. Chiba, S.; Zhang, L.; Ang, G. Y.; Hui, B. W.-Q. Org. Lett. 2010, 12, 2052
69. Iida, S.; Ohmura, R.; Togo, H. Tetrahedron 2009, 65, 6257
70. Iida, S.; Togo, H. Synlett 2008, 11, 1639
71. McCleverty, J. A.; Ninnes, C. W.; Wolochowicz, I. J. Chem. Soc., Dalton Trans. 1986, 743
72. Sato, R.; Ityoh, K.; Itoh, K.; Nishina, H.; Goto, T.; Saito, M. Chem. Lett. 1984, 1913
73. Zhou, W.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094
74. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
75. Buckle, D. R. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, UK, 1995; Vol. 3, p 1699.
76. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153
77. Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817
78. Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949
79. Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
80. Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146
81. Sprecher, M.; Kost, D. J. Am. Chem. Soc. 1994, 116, 1016
82. Katz, C. E.; Aubé, J. J. Am. Chem. Soc. 2003, 125, 13948
83. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260
84. Yao, L.; Aubé, J. J. Am. Chem. Soc. 2007, 129, 2766
85. Richard, J. P.; Amyes, T. L.; Lee, Y. G.; Jagannadham, V. J. Am. Chem. Soc. 1994, 116, 10833