Synthesis of α-diazo carbonyl compounds with the shelf-stable diazo transfer reagent nonafluorobutanesulfonyl azide

Advanced Synthesis and Catalysis

Volumn 353, Issue 4, 2011, Pages 575-579

  Chiara, Jose Luis ^a   Suárez, José Ramón ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Azides; Diazo compounds; Diazo transfer; Ketones; Sulfonyl azides

Indexed keywords

EID: 79952561917     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000846     Document Type: Article

References (91)

1. a) M. Regitz, H. Heydt, in: 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, (Ed.: A. Padwa), Wiley-Interscience, New York, 1984, pp. 393-558;
2. b) M. Kissane, A. R. Maguire, Chem. Soc. Rev. 2010, 39, 845-883;
3. c) H. M. L. Davies, J. R. Denton, Chem. Soc. Rev. 2009, 38, 3061-3071;
4. d) C. A. Merlic, A. L. Zechman, Synthesis 2003, 1137-1156;
5. e) T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091-1160. For representatives examples, see:
6. f) D. L. Whitehouse, K. H. Nelson Jr, S. N. Savinov, D. J. Austin, Tetrahedron Lett. 1997, 38, 7139-7142;
7. g) M. R. Gowravaram, M. A. Gallop, Tetrahedron Lett. 1997, 38, 6973-6976.
8. a) S. D. Burke, P. A. Grieco, Org. React. (N. Y.) 1979, 26, 361;
9. b) M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanation to Ylides, Wiley-Interscience, New York, 1998;
10. c) N. R. Candeias, C. A. M. Alfonso, Curr. Org. Chem. 2009, 13, 763-787.
11. a) T. F. Taber, Comprehensive Organic Synthesis, Vol. 3, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1990, pp 1045-1062;
12. b) M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911-935;
13. c) H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417-424.
14. A. H. Li, L. X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372.
15. a) D. F. Taber, J. C. Amedio Jr, R. G. Sherrill, J. Org. Chem. 1986, 51, 3382-3384;
16. b) K. L. Greenman, D. S. Carter, D. L. Van Vranken, Tetrahedron 2001, 57, 5219-5225;
17. c) K. L. Greenman, D. L. Van Vranken, Tetrahedron 2005, 61, 6438-6441;
18. d) S. K. J. Devine, D. L. Van Vranken, Org. Lett. 2007, 9, 2047-2049;
19. e) S. K. J. Devine, D. L. Van Vranken, Org. Lett. 2008, 10, 1909-1911;
20. f) R. Kudirka, D. L. Van Vranken, J. Org. Chem. 2008, 73, 3585-3588;
21. g) C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc. 2008, 130, 1566-1567;
22. h) S. Chen, J. Wang, Chem. Commun. 2008, 4198-4200;
23. i) W.-Y. Yu, Y.-T. Tsoi, Z. Zhou, A. S. C. Chan, Org. Lett. 2009, 11, 469-472;
24. j) R. Kudirka, S. K. J. Devine, C. S. Adams, D. L. Van Vranken, Angew. Chem. 2009, 121, 3731-3734;
25. Angew. Chem. Int. Ed. 2009, 48, 3677-3680. For the use of N-tosylhydrazones as diazocompounds precursors in Pd-catalyzed cross-couplings, see:
26. k) J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 5683-5686;
27. Angew. Chem. Int. Ed. 2007, 46, 5587-5590;
28. l) J. Barluenga, M. Tomás-Gamasa, P. Moriel, F. Aznar, C. Valdés, Chem. Eur. J. 2008, 14, 4792-4795;
29. m) J. Barluenga, M. Escribano, P. Moriel, F. Aznar, C. Valdés, Chem. Eur. J. 2009, 15, 13291-13294;
30. n) Q. Xiao, J. Ma, Y. Yang, Y. Zhang, J. Wang, Org. Lett. 2009, 11, 4732-4735;
31. o) X. Zhao, J. Jing, K. Lu, Y. Zhang, J. Wang, Chem. Commun. 2010, 1724-1726;
32. p) Z. Zhang, Y. Liu, M. Gong, X. Zhao, Y. Zhang, J. Wang, Angew. Chem. 2010, 122, 1157-1160;
33. Angew. Chem. Int. Ed. 2010, 49, 1139-1142;
34. q) L. Zhou, F. Ye, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2010, 132, 13590-13591;
35. r) J. Barluenga, M. Escribano, F. Aznar, C. Valdés, Angew. Chem. 2010, 122, 7008-7011;
36. Angew. Chem. Int. Ed. 2010, 49, 6856-6859.
37. For a recent review on the synthesis of diazo compounds, see: G. Maas, Angew. Chem. 2009, 121, 8332-8341;
38. Angew. Chem. Int. Ed. 2009, 48, 8186-8195.
39. a) M. Regitz, Synthesis 1972, 351-373;
40. b) M. Regitz, Angew. Chem. 1967, 79, 786-801;
41. Angew. Chem. Int. Ed. Engl. 1967, 6, 733-749.
42. Polymer-bound toluenesulfonyl azide: a) W. R. Roush, D. Feitler, J. Rebek, Tetrahedron Lett. 1974, 15, 1391-1392;
43. b) G. M. Green, N. P. Peet, W. A. Metz, J. Org. Chem. 2001, 66, 2509-2511.
44. 4-Dodecylbenzenesulfonyl azide: a) G. G. Hazen, L. M. Weinstock, R. Connell, F. W. Bollinger, Synth. Commun. 1981, 11, 947-956;
45. b) G. G. Hazen, F. W. Bollinger, F. E. Roberts, W. K. Russ, J. J. Seman, S. Staskiewicz, Org. Synth. 1996, 73, 144-151.
46. 4-Carboxy, 4-choloro-, 4-nitro-, and 2,4,6-trinitrobenzenesulfonyl azides (picryl azide): J. B. Hendrickson, W. A. Wolf, J. Org. Chem. 1968, 33, 3610-3618.
47. 4-Acetamidobenzenesulfonyl azide: J. S. Baum, D. A. Shook, H. M. L. Davies, H. D. Smith, Synth. Commun. 1987, 17, 1709-1716.
48. Methanesulfonyl azide (mesyl azide): D. F. Taber, R. E. Ruckle Jr, M. J. Hennessy, J. Org. Chem. 1986, 51, 4077-4078.
49. 2,4,6-Triisopropylbenzenesulfonyl azide (trisyl azide): a) R. E. Harmon, G. Wellman, S. K. Gupta, J. Org. Chem. 1973, 38, 11-16;
50. b) L. Lombardo, L. N. Mander, Synthesis 1980, 368-369.
51. Naphthalene-2-sulfonyl azide (see also ref.[9]): A. B. Khare, C. E. McKenna, Synthesis 1991, 405-406.
52. Diphenyl azidophosphate: J. M. Villalgordo, A. Enderli, A. Linden, H. Heimgartner, Helv. Chim. Acta 1995, 78, 1983-1998.
53. 2-Azido-3-ethyl-1,3-benzothiazolium tetrafluoroborate: H. Balli, R. Löw, V. Müller, H. Rempfler, A. Sezen-Gezgin, Helv. Chim. Acta 1978, 61, 97-103.
54. [16]): H. J. Monteiro, Synth. Commun. 1987, 17, 983-992.
55. Azidochloromethylene)dimethylammonium chloride: B. Kokel, H. G. Viehe, Angew. Chem. 1980, 92, 754-755;
56. Angew. Chem. Int. Ed. Engl. 1980, 19, 716-717.
57. Azidotris(diethylamino)phosphonium bromide: M. McGuiness, H. Shechter, Tetrahedron Lett. 1990, 31, 4987-4990.
58. 3): a) L. Benati, D. Nanni, P. Spagnolo, J. Org. Chem. 1999, 64, 5132-5138;
59. b) A. B. Charette, R. P. Wurz, T. Ollevier, J. Org. Chem. 2000, 65, 9252-9254;
60. c) A. B. Charette, R. P. Wurz, T. Ollevier, Helv. Chim. Acta 2002, 85, 4468-4484;
61. d) N. A. Swain, R. C. D. Brown, G. Bruton, Chem. Commun. 2002, 2042-2043;
62. e) R. P. Wurz, W. Lin, A. B. Charette, Tetrahedron Lett. 2003, 44, 8845-8848;
63. f) W. Lin, A. B. Charette, Adv. Synth. Catal. 2005, 347, 1547-1552.
64. Imidazole-1-sulfonyl azide: E. D. Goddard-Borger, R. V. Stick, Org. Lett. 2007, 9, 3797-3800.
65. 2-Azido-1,3-dimethylimidazolium chloride: M. Kitamura, N. Tashiro, T. Okauchi, Synlett 2009, 2943-2944.
66. Benzotriazole-1-yl-sulfonyl azide: A. R. Katritzky, M. El Khatib, O. Bol'shakov, L. Khelashvili, P. J. Steel, J. Org. Chem. 2010, 75, 6532-6539.
67. D. B. Ramachary, V. V. Narayana, K. Ramakumar, Tetrahedron Lett. 2008, 49, 2704-2709.
68. a) J. R. Suárez, B. Trastoy, M. E. Pérez-Ojeda, R. Marín Barrios, J. L. Chiara, Adv. Synth. Catal. 2010, 352, 2515-2520;
69. b) B. Trastoy, M. E. Pérez-Ojeda, R. Sastre, J. L. Chiara, Chem. Eur. J. 2010, 16, 3833-3841.
70. 3 for the synthesis of an organic azide, see: S. Yekta, V. Prisyazhnyuk, H.-U. Reissig, Synlett 2007, 2069-2072.
71. C. J. Cavender, V. J. Shiner, Jr., J. Org. Chem. 1972, 37, 3567-3569.
72. a) N. D. Volkov, V. P. Nazaretyan, L. M. Yagupol'skii, Zh. Org. Khim. 1982, 18, 519-525;
73. b) S. Zhu, Tetrahedron Lett. 1992, 33, 6503-6504;
74. c) S.-Z. Zhu, J. Chem. Soc. Perkin Trans. 1 1994, 2077-2081.
75. Y. Xu, Y. Wang, S. Zhu, J. Fluorine Chem. 2000, 105, 25-30.
76. S. Zhu, G. Jin, Y. Xu, Tetrahedron 2003, 59, 4389-4394.
77. I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Leito, I. A. Koppel, J. Org. Chem. 2005, 70, 1019-1028.
78. A. M. Kelly-Rowley, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 1995, 117, 3438-3447.
79. K. J. Doyle, C. J. Moody, Tetrahedron 1994, 50, 3761-3772.
80. Yu. M. Shafran, V. A. Bakulev, V. S. Mokrushin, S. G. Alekseev, Chem. Heterocycl. Compd. 1984, 20, 1038-1043.
81. Yu. Yu. Morzherin, M. Yu. Kolobov, V. S. Mokrushin, M. Brauer, E. Anders, V. A. Bakulev, Chem. Heterocycl. Compd. 2000, 36, 22-36.
82. Yu. M. Shafran, V. A. Bakulev, V. S. Mokrushin, S. G. Alekseev, A. T. Lebedev, P. A. Sharbatyan, Chem. Heterocycl. Compd. 1986, 22, 740-745.
83. G. G. Cox, D. J. Miller, C. J. Moody, E.-R. H. B. Sie, Tetrahedron 1994, 50, 3195-3212.
84. a) R. P. Wurz, A. B. Charette, Org. Lett. 2005, 7, 2313-2316;
85. b) D. Marcoux, S. Azzi, A. B. Charette, J. Am. Chem. Soc. 2009, 131, 6970-6972;
86. c) S. Levin, R. R. Nani, S. E. Reisman, Org. Lett. 2010, 12, 780-783;
87. d) D. Marcoux, V. N. G. Lindsay, A. B. Charette, Chem. Commun. 2010, 46, 910-912.
88. G. J. Roth, B. Liepold, S. G. Müller, H. J. Bestmann, Synthesis 2004, 59-62.
89. a) D. Belanger, S. Soumare, Y. L. Dory, X. Tong, Y. Zhao, Chem. Eur. J. 2009, 15, 4428-4436;
90. b) E. K. Singh, L. A. Nazarova, S. A. Lapera, L. D. Alexander, S. R. McAlpine, Tetrahedron Lett. 2010, 51, 4357-4360.
91. M. Xu, Z. Miao, B. Bernet, A. Vasella, Helv. Chim. Acta 2005, 88, 2918-2937.