A catalytic approach for the synthesis of allylic azides from aryl vinyl carbinols

Tetrahedron Letters

Volumn 54, Issue 19, 2013, Pages 2382-2385

  Srinu, G ^a   Srihari, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Azidation; Lewis acid; Nucleophilic substitution; Silylation

Indexed keywords

ALLYL ALCOHOL; ALLYL COMPOUND; AZIDE; LEWIS ACID; METAL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SALICYLALDEHYDE;

ARTICLE; CATALYSIS; DECOMPOSITION; ELECTRON; GRIGNARD REACTION; NUCLEOPHILICITY; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84875956155     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.094     Document Type: Article

References (64)

1. T. Pasinszki, M. Krebsz, and O. Wagner Curr. Org. Chem. 15 2011 1700 1719
2. E. Leemans, M. D'Hooghe, and N.D. Kimpe Chem. Rev. 111 2011 3268 3333
3. S. Brase, C. Gil, K. Knepper, and V. Zimmermann Angew. Chem., Int. Ed. 44 2005 5188 5240
4. E.F.V. Scriven, and K. Turnbull Chem. Rev. 88 1988 297 368
5. A.J. Blacker, M. Roy, S. Hariharan, A. Upare, A. Jagtap, K. Wankhade, S.K. Misra, D. Dube, S. Bhise, S. Vishwasrao, and N. Kadam Org. Process Res. Dev. 14 2010 1364 1372
6. C.E. Jakobsche, G. Peris, and S.J. Miller Angew. Chem., Int. Ed. 47 2008 6707 6711
7. P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Sheel, B. Voit, J. Pyun, J.M.J. Frechet, K.B. Sharpless, and V.V. Flkin Angew. Chem., Int. Ed. 43 2004 3928 3932
8. D.D. Diaz, S. Punna, P. Holzer, A.K. McPherson, K.B. Sharpless, V.V. Fokin, and M.G. Finn J. Polym. Sci. Part A 42 2004 4392 4403
9. A.J. Link, and D.A. Tirrell J. Am. Chem. Soc. 125 2003 11164 11165
10. B.M. Trost, and M.L. Crawley Chem. Rev. 103 2003 2921 2943
11. Y.K. Chen, A.E. Lurain, and P.J. Wash J. Am. Chem. Soc. 124 2002 12225 12231
12. A.D. Brosius, L.E. Overman, and L. Schwink J. Am. Chem. Soc. 121 1999 700 709
13. K. Burgess, L.T. Liu, and B. Pal J. Org. Chem. 58 1993 4758 4763
14. H. Kondo, H. Nakai, and T. Goto Tetrahedron 29 1973 1801 1806
15. L.V. Lee, M.L. Mitchell, S.-J. Huang, V.V. Fokin, K.B. Sharpless, and C.-H. Wong J. Am. Chem. Soc. 125 2003 9588 9589
16. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
17. (c) R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York 1 7176
18. For azide preparation from free hydroxyl groups see B.V. Rokade, S.K. Malekar, and K.R. Prabhu Chem. Commun. 48 2012 5506 5508
19. K. Kitamura, K. Tatsuya, M. Yano, and O. Okauchi Synlett 23 2012 1335 1338
20. M. Rueping, C. Vila, and U. Uria Org. Lett. 14 2012 768 771
21. A. Jaganathan, A. Garzan, D.C. Whitehead, R.J. Staples, and B. Babak Angew. Chem., Int. Ed. 50 2011 2593 2596
22. C. Amarnath, D. Surjendu, S. Sudeshna, N.N. Adarsh, and S. Amitabha Organometallics 29 2010 6619 6622
23. C. Besset, S. Chambert, B. Fenet, and Y. Queneau Tetrahedron Lett. 50 2009 7043 7047
24. A.R. Hajipour, A. Rajaei, and A.E. Ruoho Tetrahedron Lett. 50 2009 708 711
25. P.G. Cozzi, and L. Zoli Angew. Chem., Int. Ed. 47 2008 4162 4166
26. B. Sreedhar, P.S. Reddy, and N.S. Kumar Tetrahedron Lett. 47 2006 3055 3058
27. A. Jayanthi, V.K. Gumaste, and A.R.A.S. Deshmukh Synlett 2004 979 982
28. G. Vidya Sagar Reddy, G. Venkat Rao, R.V.K. Subramanyam, and D.S. Iyengar Synth. Commun. 30 2000 2233 2237
29. A.V. Malkov, P. Spoor, V. Vinader, and P. Kocovsky J. Org. Chem. 64 1999 5308 5311
30. Hughes, D. L.; Organic Reactions Hoboken, NJ, United States: John Wiley & Sons, 42, No pp. given. 1992.
31. H.M. Sampath Kumar, B.V. Subba Reddy, S. Anjaneyulu, and J.S. Yadav Tetrahedron Lett. 39 1998 7385 7388
32. M.C. Viaud, and R. Patrick Synthesis 1990 130 132
33. J. Tsuji Transition Metal Reagents and Catalysis 2000 Wiley-VCH Weinheim
34. S. Brase, and K. Banert Organic Azides Syntheses and Applications 2010 John Wiley & Sons Ltd Chichester
35. B.M. Trost, and G.C. Cook Tetrahedron Lett. 37 1996 7485 7488
36. B.M. Trost, and S.R. Pulley J. Am. Chem. Soc. 117 1995 10143 10144
37. For azide preparation from derivated hydroxy groups see T. Suzuka, K. Kosuke, and N. Takuya Polymers 3 2011 621 639
38. W. Zhou, J. Xu, Z. Liangren, and N. Jiao Synlett 2011 887 890
39. S. Fukuzawa, E. Shimizu, and S. Kikuchi Synlett 2007 2436 2438
40. Y. Uozumi, T. Suzuka, R. Kawade, and H. Takenaka Synlett 2006 2109 2113
41. G. Young Soo, J.G. Shim, and Y. Yamamoto Tetrahedron Lett. 41 2000 4193 4196
42. M. Safi, and D. Sinou Tetrahedron Lett. 32 1991 2025 2028
43. M. Safi, R. Fahrang, and D. Sinou Tetrahedron Lett. 31 1990 527 530
44. S.-I. Murahashi, Y. Tanigawa, Y. Imada, and Y. Taniguchi Tetrahedron Lett. 27 1986 227 230
45. B. Tomassy, and A. Zwierzak Synth. Commun. 1998 1201 1214
46. S.I. Murahashi, Y. Taniguchi, Y. Imada, and Y. Tanigawa J. Org. Chem. 54 1989 3292 3303
47. For few papers towards azide preparation from halides see H.A. Van Kalkeren, J. Jorick, P.J.B. Floris, L.R. Floris, and V. Delft Adv. Synth. Catal. 354 2012 1417 1421
48. L. Manjunath, D. Pradeep, and K. Prabhu Ramaiah Org. Biomol. Chem. 10 2012 2753 2759
49. M.V. Putz, M. Lazea, and L.P. Sandjo Molecules 16 2011 6603 6620
50. J. McNulty, K. Keskar, and V. Ramesh Chem. A Eur. J. 17 2011 14727 14730
51. T. Spangenberg, B. Breit, and A. Mann Org. Lett. 11 2009 261 264
52. J. Shen, R. Woodward, K. JamesPatrick, W.P. George, L. Fang, S. Duxin, X. Liu, and M. Chen J. Med. Chem. 51 2008 7417 7427
53. K. Banert, M. Hagedorn, C. Liedtke, A. Melzer, and C. Schoeffler Eur. J. Org. Chem. 2000 257 268
54. A. Koziara, and A. Zwierzak Synthesis 11 1992 1063 1065
55. R.R. Hung, J.A. Straub, and G.M. Whitesides J. Org. Chem. 56 1991 3849 3855
56. P. Srihari, D.C. Bhunia, P. Sreedhar, and J.S. Yadav Synth. Commun. 38 2008 1389 1397
57. P. Srihari, J. Shyam Sunder Reddy, D.C. Bhunia, S.S. Mandal, and J.S. Yadav Synth. Commun. 38 2008 1448 1455
58. P. Srihari, J. Shyam Sunder Reddy, S.S. Mandal, K. Satyanarayana, and J.S. Yadav Synthesis 2008 1853 1860
59. P. Srihari, D.C. Bhunia, P. Sreedhar, and J.S. Yadav Synlett 2008 1045 1049
60. (e) P. Srihari, P. Sridhar, D.C. Bhunia, J. Shyam Sunder Reddy, S.S. Mandal, and J.S. Yadav Tetrahedron Lett. 48 2007 8120 8124
61. J.S. Yadav, D.C. Bhunia, K. Vamshikrishna, and P. Srihari Tetrahedron Lett. 48 2007 8306 8310
62. The amine derivative obtained from this product was utilized as tether group in the synthesis of new class of macrocyclic antagonists. see E. Marsault, H.R. Hoveyda, M.L. Peterson, C. Saint-Louis, A. Landry, M. Vezina, L. Ouellet, Z. Wang, M. Ramaseshan, S. Beaubien, K. Benakli, S. Beauchemin, R. Deziel, T. Peeters, and G.L. Fraser J. Med. Chem. 49 2006 7190 7197
63. D. Amantini, F. Fingguelli, F. Pizzo, and L. Vaccaro J. Org. Chem. 66 2001 6734 6737
64. D. Sinol, and M. Emziane Synthesis 1986 1045 1046