Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc

Tetrahedron Letters

Volumn 55, Issue 13, 2014, Pages 2119-2122

  Li, Ya Min ^a   Shen, Yuehai ^a   Chang, Kwen Jen ^a   Yang, Shang Dong ^b  

^a KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Alkenes; Arylnitration; C H functionalization; Dihydroquinolin 2(1H) ones; Oxindoles

Indexed keywords

ACETIC ACID; ALKENE; DIHYDROQUINOLIN 2(1H)ONE; NITRO CONTAINING OXINDOLE DERIVATIVE; OXINDOLE; QUINOLINE DERIVATIVE; SILVER NITRATE; UNCLASSIFIED DRUG; ALKENE DERIVATIVE; DIHYDROQUINOLINE DERIVATIVE; FUNCTIONAL GROUP; GLYCERYL TRINITRATE;

ARTICLE; ARYLNITRATION; CHEMICAL STRUCTURE; NITRATION; COVALENT BOND; SYNTHESIS;

EID: 84896518082     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.02.043     Document Type: Article

References (60)

1. For reviews, see: C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209
2. H. Lin, and S.J. Danishefsky Angew. Chem., Int. Ed. 42 2003 36
3. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748
4. G.S. Singh, and Z.Y. Desta Chem. Rev. 112 2012 6104
5. K. Shen, X. Liu, L. Lin, and X. Feng Chem. Sci. 3 2012 327
6. R. Dalpozzo, G. Bartoli, and G. Bencivenni Chem. Soc. Rev. 41 2012 7247
7. N.R. Ball-Jones, J.J. Badillo, and A.K. Franz Org. Biomol. Chem. 10 2012 5165
8. L. Hong, and R. Wang Adv. Synth. Catal. 355 2013 1023
9. For recent reviews, see: F. Zhou, Y.-L. Liu, and J. Zhou Adv. Synth. Catal. 352 2010 1381
10. J.E.M.N. Klein, and R.J.K. Taylor Eur. J. Org. Chem. 2011 6821
11. for selected examples, see: E.J. Hennessy, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 12084
12. A. Pinto, Y. Jia, L. Neuville, and J. Zhu Chem. Eur. J. 13 2007 961
13. Y.-K. Jia, and E.P. Kündig Angew. Chem., Int. Ed. 48 2009 1636
14. A. Perry, and J.K. Taylor Chem. Commun. 2009 3249
15. S. Ueda, T. Okada, and H. Nagasawa Chem. Commun. 2010 2462
16. H.-L. Wei, T. Piou, J. Dufour, L. Neuville, and J. Zhu Org. Lett. 13 2011 2244
17. P. Tolstoy, S.X.Y. Lee, C. Sparr, and S.V. Ley Org. Lett. 14 2012 4810
18. A. Beyer, J. Buendia, and C. Bolm Org. Lett. 14 2012 3948
19. D.C. Fabry, M. Stodulski, S. Hoerner, and T. Gulder Chem. Eur. J. 18 2012 10834
20. T. Piou, L. Neuville, and J. Zhu Angew. Chem., Int. Ed. 51 2012 11561
21. G. An, W. Zhou, G. Zhang, H. Sun, J. Han, and Y. Pan Org. Lett. 12 2010 4482
22. S. Jaegli, J. Dufour, H. Wei, T. Piou, X. Duan, J. Vors, L. Neuville, and J. Zhu Org. Lett. 12 2010 4498
23. T. Wu, X. Mu, and G. Liu Angew. Chem., Int. Ed. 50 2011 12578
24. X. Mu, T. Wu, H. Wang, Y. Guo, and G. Liu J. Am. Chem. Soc. 134 2012 878
25. W.-T. Wei, M.-B. Zhou, J.-H. Fan, W. Liu, R.-J. Song, Y. Liu, M. Hu, P. Xie, and J.-H. Li Angew. Chem., Int. Ed. 52 2013 3638
26. Y.-M. Li, M. Sun, H.-L. Wang, Q.-P. Tian, and S.-D. Yang Angew. Chem., Int. Ed. 52 2013 3972
27. J. Xie, P. Xu, H. Li, Q. Xue, H. Jin, Y. Cheng, and C. Zhu Chem. Commun. 2013 5672
28. X.-H. Wei, Y.-M. Li, A.-X. Zhou, T.-T. Yang, and S.-D. Yang Org. Lett. 15 2013 4158
29. H. Wang, L.-N. Guo, and X.-H. Duan Adv. Synth. Catal. 355 2013 2222
30. S.-L. Zhou, L.-N. Guo, H. Wang, and X.-H. Duan Chem. Eur. J. 19 2013 12970
31. Y. Yuan, T. Shen, K. Wang, and N. Jiao Chem. Asian J. 8 2013 2932
32. M.-B. Zhou, R.-J. Song, X.-H. Ouyang, Y. Liu, W.-T. Wei, G.-B. Deng, and J.-H. Li Chem. Sci. 4 2013 2690
33. Y. Meng, L.-N. Guo, H. Wang, and X.-H. Duan Chem. Commun. 2013 7540
34. X. Li, X. Xu, P. Hu, X. Xiao, and C. Zhou J. Org. Chem. 78 2013 7343
35. K. Matcha, R. Narayan, and A.P. Antonchick Angew. Chem., Int. Ed. 52 2013 7985
36. H. Wang, L.-N. Guo, and X.-H. Duan Org. Lett. 15 2013 5254
37. Y.-M. Li, X.-H. Wei, X.-A. Li, and S.-D. Yang Chem. Commun. 2013 11701
38. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH New York
39. H. Feuer, and A.T. Nielson Nitro Compounds: Recent Advances in Synthesis and Chemistry 1990 VCH Weinheim
40. A.G.M. Barrett, and G.G. Graboski Chem. Rev. 86 1986 751
41. For selected papers on nitration reactions, see: H. Shechter, F. Conrad, A.L. Daulton, and R.B. Kaplan J. Am. Chem. Soc. 74 1952 3052
42. E.J. Corey, and H. Estreicher J. Am. Chem. Soc. 100 1978 6294
43. T. Hayama, S. Tomoda, Y. Takeuchi, and Y. Nomura Tetrahedron Lett. 23 1982 4733
44. G.A. Olah, P. Ramaiah, C.B. Rao, S. Graham, R. Golam, N.J. Trivedi, and J.A. Olah J. Am. Chem. Soc. 115 1993 7246
45. P.J. Campos, B. García, and M.A. Rodríguez Tetrahedron Lett. 41 2000 979
46. I. Jovel, S. Prateeptongkum, R. Jackstell, N. Vogl, C. Weckbecker, and M. Beller Adv. Synth. Catal. 350 2008 2493
47. N. Kornblum, B. Taub, and H.E. Ungnade J. Am. Chem. Soc. 76 1954 3209
48. N. Kornblum, and J.W. Powers J. Org. Chem. 22 1957 455
49. T.E. Stevens, and W.D. Emmons J. Am. Chem. Soc. 80 1958 338
50. H. Suzuki, and T. Mori J. Org. Chem. 62 1997 6498
51. J.-L. Grenier, J.-P. Catteau, and P. Cotelle Synth. Commun. 29 1999 1201
52. L. Grossi, P.C. Montevecchi, and S. Strazzari Eur. J. Org. Chem. 2001 741
53. L. Grossi, and P.C. Montevecchi Chem. Eur. J. 8 2002 380
54. K. Jayakanthan, K.P. Madhusudanan, and Y.D. Vankar Tetrahedron 60 2004 397
55. S. Saito, and Y. Koizumi Tetrahedron Lett. 46 2005 4715
56. B.P. Fors, and S.L. Buchwald J. Am. Chem. Soc. 131 2009 12898
57. G.K.S. Prakash, and T. Mathew Angew. Chem. Int. Ed. 49 2010 1726
58. T. Taniguchi, T. Fujii, and H. Ishibashi J. Org. Chem. 75 2010 8126
59. T. Taniguchi, A. Yajima, and H. Ishibashi Adv. Synth. Catal. 353 2011 2643
60. S. Manna, S. Maity, S. Rana, S. Agasti, and D. Maiti Org. Lett. 14 2012 1736