Direct oxidative conversion of methylarenes into aromatic nitriles

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4194-4197

  Tsuchiya, Daisuke ^a   Kawagoe, Yuhsuke ^a   Moriyama, Katsuhiko ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882777540     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401906q     Document Type: Article

References (62)

1. Sandler, S. R.; Karo, W. Nitriles (Cyanides). In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1983; Vol. 12-I of Organic Chemistry, Chapter 17.
2. Fabiani, M. E. Drug News Perspect. 1999, 12, 207
3. Friedrick, K.; Wallensfels, K. The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Wiley-Interscience: New York, 1970.
4. North, M. Comprehensive Organic Functional Group Transformation; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford; 1995.
5. Murahashi, S.-I. Synthesis from Nitriles with Retention of the Cyano Group. Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2004; Vol. 19, pp 345-402.
6. Collier, S. J.; Langer, P. Application of Nitriles as Reagents for Organic Synthesis with Loss of the Nitrile Functionality. Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2004; Vol. 19, pp 403-425.
7. Reisner, D. B.; Coring, E. C. Organic Synthesis; Wiley: New York, 1963; Collect. Vol. IV, p 144.
8. Krynitsy, J. A.; Carhart, H. W. Organic Synthesis; Wiley: New York, 1963; Collect. Vol. IV, p 436
9. Humber, J. G.; Davis, M. A. Can. J. Chem. 1966, 44, 2113
10. Yamato, E.; Sugasawa, S. Tetrahedron Lett. 1970, 4348
11. Lehnert, W. Tetrahedron Lett. 1971, 1501
12. Campagna, F.; Caroti, A.; Casini, G. Tetrahedron Lett. 1977, 1813
13. Mai, K.; Patal, G. Tetrahedron Lett. 1986, 27, 2203
14. Claremon, D. A.; Phillips, B. Tetrahedron Lett. 1988, 29, 2155
15. Nemoto, H.; Kubota, Y.; Yamamoto, Y. J. Org. Chem. 1990, 55, 4515
16. Sznaidman, M. L.; Crasto, C.; Hecht, S. M. Tetrahedron Lett. 1993, 34, 1581
17. Xue, C. B.; Degrado, W. F. Tetrahedron Lett. 1995, 61, 6486 and references cited therein
18. Heck, M.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1996, 61, 6486
19. Nakajima, N.; Ubukata, M. Tetrahedron Lett. 1997, 38, 2099
20. Bose, D. S.; Jayalakshmi, B.; Goud, P. R. Synthesis 1999, 1724
21. Bose, D. S.; Jayalakshmi, B. Synthesis 1999, 64
22. Kuo, C.; Zhu, J.; Wu, J.; Chu, C.; Yao, C.; Shia, K. Chem. Commun. 2007, 301
23. Larock, R. C. Comprehensive Organic Transformation; VCH Publishers: Weinheim, 1989; pp 976-993.
24. Sandmeyer, T. Ber. 1884, 17 (1633) 2650
25. Sharman, W. M.; Van Lier, J. E. In Porphyrin Handbook; Kadish, E.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2003; Vol. 15, p 1.
26. Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508
27. Littke, A.; Soumeillant, M.; Kaltenbach, R. F., III; Cherney, R. J.; Tarby, C. M.; Kiau, S. Org. Lett. 2007, 9, 1711
28. Martin, M. T.; Liu, B.; Cooley, B. E., Jr.; Eaddy, J. F. Tetrahedron Lett. 2007, 48, 2555
29. Nandurkar, N. S.; Bhanage, B. M. Tetrahedron 2008, 64, 3655
30. Iqbal, Z.; Lyubimtsev, A.; Hanack, M. Synlett 2008, 2287
31. Chen, G.; Weng, J.; Zheng, Z.; Zhu, X.; Cai, Y.; Cai, J.; Wan, Y. Eur. J. Org. Chem. 2008, 3524
32. Schareina, T.; Zapf, A.; Cotte, A.; Müller, N.; Beller, M. Synthesis 2008, 3351
33. Buono, F. G.; Chidambaram, R.; Mueller, R. H.; Waltermire, R. E. Org. Lett. 2008, 10, 5325
34. Chattopadhyay, K.; Dey, R.; Ranu, B. C. Tetrahedron Lett. 2009, 50, 3164
35. DeBlase, C.; Leadbeater, N. E. Tetrahedron 2010, 66, 1098
36. Yan, G.; Kuang, C.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 1052
37. Yu, H.; Richey, R. N.; Miller, W. D.; Xu, J.; May, S. A. J. Org. Chem. 2011, 76, 665
38. Ushkov, A. V.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 10999
39. Yeung, P. Y.; Tsang, C. P.; Kwong, F. Y. Tetrahedron Lett. 2011, 52, 7038
40. Hajipour, A. R.; Rafiee, F.; Ruoho, A. E. Tetrahedron 2012, 53, 526
41. Zhang, D.; Sun, H.; Zhang, L.; Zhou, Y.; Li, C.; Jiang, H. Chem. Commun. 2012, 48, 2909
42. Gerhard, L. Ber. 1967, 100, 2719
43. Gerhard, L. Org. Synth. 1970, 50, 52
44. Tamura, Y.; Kita, Y.; Kawasaki, T. J. Synth. Org. Chem. 1980, 38, 891
45. Ushijima, S.; Togo, H. Synlett 2010, 1562
46. Ushijima, S.; Moriyama, K.; Togo, H. Tetrahedron 2011, 67, 958
47. Ushijima, S.; Togo, H. Synlett 2010, 1067
48. Ushijima, S.; Moriyama, K.; Togo, H. Tetrahedron 2012, 68, 4588
49. Ishii, G.; Moriyama, K.; Togo, H. Tetrahedron Lett. 2011, 52, 2402
50. Ishii, G.; Harigae, R.; Moriyama, K.; Togo, H. Tetrahedron 2013, 69, 1462
51. Review: Lücke, B.; Narayana, K. V.; Martin, A.; Jähnisch, K. Adv. Synth. Catal. 2004, 346, 1407 and references cited therein
52. Zhou, W.; Zhang, L.; Jiao, N. Angw. Chem. Int. Ed. 2009, 48, 7094
53. Iida, S.; Togo, H. Synlett 2008, 1639
54. Iida, S.; Ohmura, R.; Togo, H. Tetrahedron 2009, 65, 6257
55. Wohl, A. Ber. 1919, 52, 51
56. Ziegler, K. Ann. 1942, 551, 30
57. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, p 145.
58. Iida, S.; Togo, H. Synlett 2006, 2633
59. Iida, S.; Togo, H. Synlett 2007, 407
60. Iida, S.; Togo, H. Tetrahedron 2007, 63, 8274
61. Okamoto, K.; Eger, B. T.; Nishuno, T.; Kondo, S.; Pai, E. F.; Nishino, T. J. Biol. Chem. 2003, 278, 1848
62. Canivel, J.; Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11, 1733