Nonafluorobutanesulfonyl azide: A shelf-stable diazo transfer reagent for the synthesis of azides from primary amines

Advanced Synthesis and Catalysis

Volumn 352, Issue 14-15, 2010, Pages 2515-2520

  Suárez, José Ramón ^a   Trastoy, Beatriz ^a   Pérez Ojeda, M Eugenia ^b   Marín Barrios, Rubén ^a   Chiara, Jose Luis ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

amines; azides; click chemistry; copper; diazo transfer

Indexed keywords

EID: 78349231953     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000417     Document Type: Article

References (66)

1. E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297
2. S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320
3. Angew. Chem. Int. Ed. 2005, 44, 5188
4. Organic Azides: Synthesis and Applications, (Eds.:, S. Bräse, K. Banert,), John Wiley & Sons Ltd, Chichester, 2010.
5. M. Köhn, R. Breinbauer, Angew. Chem. 2004, 116, 3168
6. Angew. Chem. Int. Ed. 2004, 43, 3106
7. N. J. Agard, J. M. Baskin, J. A. Prescher, A. Lo, C. R. Bertozzi, ACS Chem. Biol. 2006, 1, 644
8. V. V. Fokin, ACS Chem. Biol. 2007, 2, 775
9. R. J. Pieters, D. T. S. Rijkers, R. M. J. Liskamp, QSAR Comb. Sci. 2007, 26, 1181
10. E. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108
11. Angew. Chem. Int. Ed. 2009, 48, 6974
12. J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272.
13. W. H. Binder, C. Kluger, Curr. Org. Chem. 2006, 10, 1791
14. J.-F. Lutz, Angew. Chem. 2007, 119, 1036
15. Angew. Chem. Int. Ed. 2007, 46, 1018
16. W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952
17. R. K. Iha, K. L. Wooley, A. M. Nystrom, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620
18. F. Santoyo-González, F. Hernández-Mateo, Chem. Soc. Rev. 2009, 38, 3449
19. P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338.
20. R. Huisgen, R. Knorr, L. Moebius, G. Szeimies, Chem. Ber. 1965, 98, 4014
21. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057
22. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708
23. Angew. Chem. Int. Ed. 2002, 41, 2596
24. M. Meldal, C. W. Tornoe, Chem. Rev. 2008, 108, 2952.
25. C. J. Cavender, V. J. Shiner Jr, J. Org. Chem. 1972, 37, 3567.
26. A. Vasella, C. Witzig, J. L. Chiara, M. Martín-Lomas, Helv. Chim. Acta 1991, 74, 2073.
27. P. B. Alper, S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029
28. P. T. Nyffeler, C.-H. Liang, K. M. Koeller, C.-H. Wong, J. Am. Chem. Soc. 2002, 124, 10773.
29. S. A. Fleming, Tetrahedron 1995, 51, 12479.
30. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056
31. Angew. Chem. Int. Ed. 2001, 40, 2004.
32. J. Zaloom, D. C. Roberts, J. Org. Chem. 1981, 46, 5173.
33. A. Titz, Z. Radic, O. Schwardt, B. Ernst, Tetrahedron Lett. 2006, 47, 2383.
34. B. Trastoy, M. E. Pérez-Ojeda, R. Sastre, J. L. Chiara, Chem. Eur. J. 2010, 16, 3833.
35. E. Rikowski, H. C. Marsmann, Polyhedron 1997, 16, 3357.
36. For recent alternative routes to 2 via nucleophilic substitution with varying degrees of cage rearrangements, see
37. Z. Ge, D. Wang, Y. Zhou, H. Liu, S. Liu, Macromolecules 2009, 42, 2903 - 2910
38. V. Ervithayasuporn, X. Wang, Y. Kawakami, Chem. Commun. 2009, 5130
39. S. Fabritz, D. Heyl, V. Bagutski, M. Empting, E. Rikowski, H. Frauendorf, I. Balog, W.-D. Fessner, J. J. Schneider, O. Avrutina, H. Kolmar, Org. Biomol. Chem. 2010, 8, 2212
40. D. Heyl, E. Rikowski, R. C. Hoffmann, J. J. Schneider, W.-D. Fessner, Chem. Eur. J. 2010, 16, 5544.
41. J. H. Boyer, R. Moriarty, B. de B. Darwent, P. A. S. Smith, Chem. Eng. News 1964, 42, 6
42. P. A. S. Smith, The Chemistry of Open-Chain Organic Nitrogen Compounds, Vol. II, Derivatives of Oxidized Nitrogen: Hydrazines to Nitrates, W. A. Benjamin, New York, 1966.
43. W. A. Sheppard, J. Am. Chem. Soc. 1965, 87, 2410.
44. J. Högermeier, H.-U. Reissig, Adv. Synth. Catal. 2009, 351, 2747 - 2763.
45. N. D. Volkov, V. P. Nazaretyan, L. M. Yagupol'skii, Zh. Org. Khim. 1982, 18, 519
46. S. Zhu, Tetrahedron Lett. 1992, 33, 6503
47. S.-Z. Zhu, J. Chem. Soc. Perkin Trans. 1 1994, 2077.
48. Y. Xu, G. Xu, S. Zhu, G. Zhu, Y. Jia, Q. Huang, J. Fluorine Chem. 1999, 96, 79
49. S.-Z. Zhu, G.-F. Jin, J.-W. Zhao, J. Fluorine Chem. 2003, 120, 65
50. Y. Xu, S. Zhu, Synthesis 2001, 690
51. S.-Z. Zhu, P. He, J.-W. Zhao, X. Cai, J. Fluorine Chem. 2004, 125, 445
52. P. He, S.-Z. Zhu, J. Fluorine Chem. 2005, 126, 113.
53. S. Zhu, P. He, Tetrahedron 2005, 61, 5679.
54. Y. Xu, S. Zhu, Tetrahedron 1999, 55, 13725
55. Y. Xu, S. Zhu, Tetrahedron 2001, 57, 4337
56. S. Zhu, G. Jin, P. He, Y. Xu, Q. Huang, Tetrahedron Lett. 2003, 44, 8717.
57. S. Yekta, V. Prisyazhnyuk, H.-U. Reissig, Synlett 2007, 2069.
58. H. S. G. Beckmann, V. Wittmann, Org. Lett. 2007, 9, 1
59. N. G. Angelo, P. S. Arora, J. Org. Chem. 2007, 72, 7963
60. C.-T. Lee, S. Huang, B. H. Lipshutz, Adv. Synth. Catal. 2009, 351, 3139.
61. For recent examples of intramolecular copper-catalyzed azide-alkyne 1,3-dipolar cycloadditions, see
62. A. Ray, K. Manoj, M. M. Bhadbhade, R. Mukhopadhyay, A. Bhattacharjya, Tetrahedron Lett. 2006, 47, 2775
63. S. Chandrasekhar, C. L. Rao, C. Nagesh, C. R. Reddy, B. Sridhar, Tetrahedron Lett. 2007, 48, 5869
64. S. Ç. Jarosz, B. Lewandowski, A. Listkowski, Synthesis 2008, 2008, 913.
65. E. D. Goddard-Borger, R. V. Stick, Org. Lett. 2007, 9, 3797
66. N. M. Smith, M. J. Greaves, R. Jewell, M. W. D. Perry, M. J. Stocks, J. P. Stonehouse, Synlett 2009, 1391.