One-pot synthesis of carbamoyl azides directly from primary alcohols and oxidation of secondary alcohols to ketones using iodobenzene dichloride in combination with sodium azide

Advanced Synthesis and Catalysis

Volumn 351, Issue 14-15, 2009, Pages 2342-2350

  Li, Xiao Qiang ^a   Wang, Wei Kun ^a   Zhang, Chi ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Alcohols; Carbamoyl azides; Hypervalent compounds; Iodobenzene dichloride; Oxidation; Sodium azide

Indexed keywords

EID: 70350589015     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900428     Document Type: Article

References (82)

1. a) R. C. Larock, Comprehensive Organic Transformations, 2nd edn.; Wiley, New York, 1999;
2. b) G. Tojo, M. Fernández, Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice, Springer, New York, 2006.
3. a) M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, R J. Reider, J. Org. Chem. 1999, 64, 2564, and references therein;
4. b) H. Tohma, S. Takizawa, T. Maegawa, Y. Kita, Angew. Chem. 2000, 112, 1362;
5. Angew. Chem. Int. Ed. 2000, 39, 1306;
6. c) H. Tohma, T. Maegawa, S. Takizawa, Y. Kita, Adv. Synth. Catal. 2002, 344, 328.
7. a) J. N Milovanović, M. Vasojević, S. Gojković, J. Chem. Soc. Perkin Trans. 2 1991,1231;
8. b) H. Tohma, T. Maegawa, Y. Kita, Synlett 2003, 723;
9. c) J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, J. Am. Chem. Soc. 2005, 127, 10840;
10. d) N. Moria, H. Togo, Tetrahedron 2005, 61, 5915;
11. e) N. A. Owston, A. J. Parker, J. M. J. Williams, Chem. Commun. 2008, 624.
12. a) C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317. 790;
13. b) L. U. Nordstrøm, H. Vogt, R. Madsen, J. Am. Chem. Soc. 2008, 130, 17672;
14. c) T. Zweifel, J.-V. Naubron, H. Grützmacher, Angew. Chem. Int. Ed. 2009, 48, 559;
15. d) A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, Org. Lett. 2009,11, 2667.
16. T. Oishi, K. Yamaguchi, N Mizuno, Angew. Chem. 2009,121, 6404;
17. Angew. Chem. Int. Ed. 2009, 48, 6286.
18. a) C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789;
19. Angew. Chem. Int. Ed. 2008, 47, 8661.
20. T. Naota, S.-I. Murahashi, Synlett 1991, 693.
21. C. Gunanathan, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2009,131, 3146.
22. A. J. Blacker, M. M. Farah, M. I. Hall, S. R Marsden, O. Saidi, J. M. J. Williams, Org. Lett. 2009,11, 2039.
23. a) E. Lieber, R. L. Minnis. Jr., C. N. R. Rao, Chem. Rev. 1965, 65, 377;
24. b) E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297;
25. c) S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320;
26. Angew. Chem. Int. Ed. 2005, 44, 5188.
27. a) E. Oliveri-Mandala, E. Calderaro, Gazz. Chim. Ital. 1913, 43, 538;
28. b) E. Oliveri-Mandala, F. Noto, Gazz. Chim. Ital. 1913, 43, 514.
29. a) W. L. Lipschitz, J. Am. Chem. Soc. 1944, 66, 658;
30. b) F. L. Scott, A. Koczarski, J. Reilly, Nature 1952,170, 922.
31. a) T. Curtius, A. Burkhardt, J. Prakt. Chem. 1898,116, 205;
32. b) T. Curtius, F. Schmidt, J. Prakt. Chem. 1923, 213,177.
33. a) T. Curtius, J. Prakt. Chem. 1894, 50, 275;
34. b) P. Laszlo, E. Polla, Tetrahedron Lett. 1984, 25, 3701;
35. c) G. K. S. Prakash, P. S. Iyer, M. Arvanaghi, G. A. Olah, J. Org. Chem. 1983, 48, 3358;
36. d) A. R. Katritzky, K. Widyan, K. Kirichenko, J. Org. Chem. 2007, 72, 5802.
37. For phenyldichlorophosphate, see : a) J. M. Lago, A. Arrieta, C. Palomo, Synth. Commun. 1983,13, 289; for ethyl chloroformate, see:
38. 2-DMF, see:
39. 3P, see :
40. d) P. Froeyen, Phosphorus Sulfur Silicon Relat. Elem. 1994, 89, 57;
41. e) P. Froeyen, Synth. Commun. 1996, 26, 4549; for diphenylphosphoryl azide (DPPA), see:
42. f) H. Shao, M. Colucci, S. Tong, H. Zhang, A. L. Castelhano, Tetrahedron Lett. 1998, 39, 7235; For triphosgene, see:
43. g) V. K. Gumaste, B. M. Bhawal, A. R. A. S. Deshmukh, Tetrahedron Lett. 2002, 43, 1345; for cyanuric chloride, see:
44. h) B. P. Bandgar, S. S. Pandit, Tetrahedron Lett. 2002, 43, 3413.
45. 3, see: a) J. G. Lee, K. H. Kwak, Tetrahedron Lett. 1992, 33, 3165;
46. 2, see:
47. 3, see:
48. d) L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem. 2003, 68, 9453; for polystyrene supported diazidoiodate, see :
49. 3, see :
50. 3, see:
51. 3, see:
52. 3, see:
53. i) X.-Q. Li, X.-F. Zhao, C. Zhang, Synthesis 2008, 2589.
54. a) E. García-Egido, M. Fernández-Suárez, L. Muñoz, J. Org. Chem. 2008, 73, 2909;
55. b) V. K. Gumaste, A. R. A. S. Deshmukh, Tetrahedron Lett. 2004, 45, 6571.
56. a) X.-F. Zhao, C. Zhang, Synthesis 2007, 551; for a recyclable cyclic iodine (III) reagent having an I-Cl bond in the selective oxidation of alcohols, see:
57. b)X.-Q. Li, C. Zhang, Synthesis 2009,1163;
58. c) J. Yu, C. Zhang, Synthesis 2009, 2324.
59. a) C. Willgerodt, J. Prakt. Chem. 1886, 33, 154;
60. b) D. F Banks, Chem. Rev. 1966, 66, 243;
61. c) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123;
62. d) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997;
63. e) P. J. Stang, V. V. Zhdankin, Chem. Rev. 2002, 102, 2523;
64. f) Hypervalent Iodine Chemistry, (Ed.: T Wirth), Springer-Verlag, Berlin, Heidelberg, 2003;
65. g) T. Wirth, Angew. Chem. 2005,117, 3722;
66. Angew. Chem. Int. Ed. 2005, 44, 3656;
67. h) E. D. Matveeva, M. V. Proskurnina, N S. Zefirov, Heteroatom Chem. 2006,17, 595;
68. i) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299;
69. j) V. V. Zhdankin, ARKIVOC 2009, 1.
70. J. Wicha, A. Zarecki, M. Kocór, Tetrahedron Lett. 1973, 14, 3635.
71. [16i] TEMPO is not involved during the direct conversion of primary alcohols to their carbamoyl azides.
72. V. J. Bauer, W. J. Fanshawe, S. D. R. Safir, J. Org. Chem. 1966, 31, 3440.
73. W Kuhn, U. S. Patent 6,624,330, 2003.
74. 2, see: a) M. Arimoto, H. Yamaguchi, E. Fujita, M. Ochiai, Y Nagao, Tetrahedron Lett. 1987, 28, 6289;
75. b) N. S. Zefirov, S. O Safronov, A. A. Kaznacheev, V. V. Zhdankin, J. Org. Chem. USSR, 1990, 26, 1633;
76. c) P. Magnus, J. Lacour, J. Am. Chem. Soc. 1992,114, 767.
77. Chloride and azide anions were analyzed quantitatively using Dionex DX-120 Ion Chromatography System.
78. Aldrich/ACD Library of FT NMR Spectra.
79. S. Hajra, M. Bhowmick, B. Maji, D. Sinha, J. Org. Chem. 2007, 72, 4872.
80. G A. Molander, C.-S. Yun, M. Ribagorda, B. Biolatto, J. Org. Chem. 2003, 68, 5534.
81. G. J. Bodwell, J. Li, D. O. Miller, Tetrahedron 1999, 55, 12939.
82. J. Hora, Recl. J. R. Neth. Chem. Soc. 1976, 95, 45.