Transformation of aromatic bromides into aromatic nitriles via formations of grignard reagents and their DMF adducts

Tetrahedron Letters

Volumn 52, Issue 18, 2011, Pages 2404-2406

  Ishii, Genki ^a   Moriyama, Katsuhiko ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; BROMIDE; IODINE; MAGNESIUM; N,N DIMETHYLFORMAMIDE; NITRILE;

ARTICLE; DRUG STRUCTURE; DRUG TRANSFORMATION; GRIGNARD REACTION; ROOM TEMPERATURE;

EID: 79953281700     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.110     Document Type: Article

References (55)

1. S.R. Sandier, and W. Karo Organic Functional Group Preparations 1983 Academic Press San Diego Vol. 12-I, Chapter 17
2. M.E. Fabiani Drug News Perspect. 12 1999 207
3. K. Friedrick, and K. Wallensfels Z. Rappoport, The Chemistry of the Cyano Group 1970 Wiley-Interscience New York
4. M. North A.R. Katritzky, O. Meth-Cohn, C.W. Rees, Comprehensive Organic Functional Group Transformation 1995 Pergamon Oxford
5. S.-I. Murahashi Sci. Synth. 19 2004 345 402 Georg Thieme
6. S.J. Collier, and P. Langer Sci. Synth. 19 2004 403 425 Georg Thieme
7. R.C. Larock, Comprehensive Organic Transformation 1989 VCH Publishers USA pp.976-993
8. K. Ouchaou, D. Georgin, and F. Taran Synlett 2010 2083
9. A.R. Katritzky, G.F. Zhang, and W.Q. Fan Org. Prep. Proced. Int. 25 1993 315
10. H.G. Forey, and D.R.J. Dalton Chem. Soc., Chem. Commun. 1973 628
11. V.P. Kukhar, and V.I. Pasternak Synthesis 1974 628
12. H. Shinozaki, M. Imaizumi, and M. Tajima Chem. Lett. 1983 929
13. H.M. Meshram Synthesis 1992 943
14. J.A. Findlay, and C.S. Tang Can. J. Chem. 45 1967 1014
15. J.K. Augustine, R.N. Atta, B.K. Ramappa, and C. Boodappa Synlett 2009 3378
16. T. Sandmeyer Ber. 17 1633 1884 2650
17. K.W. Rosenmund Chem. Ber. 52 1916 1749
18. J. Lindley Tetrahedron 40 1984 1433
19. W.M. Sharman, and J.E. Van Lier E. Kadish, K.M. Smith, R. Guilard, Porphyrin Handbook 2003 Academic Press New York 1, Vol. 15
20. S.A. Weissman, D. Zewge, and C. Chen J. Org. Chem. 70 2005 1508
21. A. Littke, M. Soumeillant, R.F. Kaltenbach III, R.J. Cherney, C.M. Tarby, and S. Kiau Org. Lett. 9 2007 1711
22. M.T. Martin, B. Liu, B.E. Cooley Jr., and J.F. Eaddy Tetrahedron Lett. 48 2007 2555
23. N.S. Nandurkar, and B.M. Bhanage Tetrahedron 64 2008 3655
24. Z. Iqbal, A. Lyubimtsev, and M. Hanack Synlett 2008 2287
25. G. Chen, J. Weng, Z. Zheng, X. Zhu, Y. Cai, J. Cai, and Y. Wan Eur. J. Org. Chem. 2008 3524
26. T. Schareina, A. Zapf, A. Cotte, N. Müller, and M. Beller Synthesis 2008 3351
27. F.G. Buono, R. Chidambaram, R.H. Mueller, and R.E. Waltermire Org. Lett 10 2008 5325
28. K. Chattopadhyay, R. Dey, and B.C. Ranu Tetrahedron Lett. 50 2009 3164
29. G. Yan, C. Kuang, Y. Zhang, and J. Wang Org. Lett 12 2010 1052
30. C. DeBlase, and N.E. Leadbeater Tetrahedron 66 2010 1098
31. X. Chen, X.-S. Hao, C.E. Goodhue, and J.-Q. Yu J. Am. Chem. Soc. 128 2006 6790
32. X. Jia, D. Yang, S. Zhang, and J. Cheng Org. Lett. 11 2009 4716
33. J. Kim, and S. Chang J. Am. Chem. Soc. 132 2010 10272
34. H. Do, and O. Daugulis Org. Lett. 12 2010 2517
35. B.V.S. Reddy, Z. Begum, Y.J. Reddy, and J.S. Yadav Tetrahedron Lett. 51 2010 3334
36. G. Yan, C. Kuang, Y. Zhang, and J. Wang Org. Lett. 12 2010 1052
37. P. Anbarasan, H. Neumann, and M. Beller Chem. Eur. J. 16 2010 4725
38. Reviews: H. Togo, and S. Iida Synlett 2006 2159
39. H.J. Togo Synth. Org. Chem. Jpn. 66 2008 652
40. N. Mori, and H. Togo Synlett 2004 880
41. N. Mori, and H. Togo Synlett 2005 1456
42. N. Mori, and H. Togo Tetrahedron 61 2005 5915
43. M. Ishihara, and H. Togo Synlett 2006 227
44. S. Iida, and H. Togo Synlett 2006 2633
45. M. Ishihara, and H. Togo Tetrahedron 63 2007 1474
46. S. Iida, and H. Togo Tetrahedron 63 2007 8274
47. S. Iida, and H. Togo Synlett 2007 407
48. S. Iida, and H. Togo Synlett 2008 1639
49. S. Iida, R. Ohmura, and H. Togo Tetrahedron 65 2009 6257
50. A. Misono, T. Osa, and S. Koda Bull. Chem. Soc. Jpn. 39 1966 854
51. S. Talukdar, J. Hsu, T. Chou, and J. Fang Tetrahedron Lett. 42 2001 1103
52. S. Ushijima, and H. Togo Synlett 2010 1067
53. S. Ushijima, and H. Togo Synlett 2010 1562
54. 3) δ = 21.7, 109.2, 119.1, 129.7, 131.9, 143.6.
55. A. Krasovskiy, and P. Knochel Angew. Chem., Int. Ed. 43 2004 3333