Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3·;7H2O/NaI system

Journal of Organic Chemistry

Volumn 73, Issue 5, 2008, Pages 1919-1924

  Bartoli, Giuseppe ^c   Di Antonio, Giustino ^a,b   Giovannini, Riccardo ^b   Giuli, Sandra ^a   Lanari, Silvia ^a   Paoletti, Melissa ^a   Marcantoni, Enrico ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b Boehringer Ingelheim Italia SpA   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDO GROUP; LEWIS ACID;

ACETONITRILE; FUNCTIONAL GROUPS; MICROWAVES; NITROGEN; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINES;

ACETONITRILE; AMINE; AZIDE; CERIUM CHLORIDE; CHLORIDE; LEWIS ACID; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DECOMPOSITION; MICROWAVE RADIATION; REACTION TIME; REDUCTION; ROOM TEMPERATURE;

AMINES; AZIDES; CERIUM; MAGNETIC RESONANCE SPECTROSCOPY; SODIUM IODIDE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; WATER;

EID: 41149117670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7024288     Document Type: Article

References (94)

1. Hollmann, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem. Asian J. 2007, 2, 403-410.
2. Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785-7811.
3. (a) Vidya Sagar Reddy, G.; Venkat Rao, G.; Subramanyam, R. V. K.; Iyengar, D. S. Synth. Commun. 2000, 30, 2233-2237.
4. (b) Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190-192.
5. Haight, G. P.; Jones, L. L. J. Chem. Educ. 1987, 64, 271-273.
6. Hughes, D. L. Org. React. 1992, 42, 335-656.
7. (a) Kurada, K.; Hayashi, Y.; Mukaiyama, T. Tetrahedron 2007, 63, 6358-6364.
8. (b) Lindsley, C. W.; Zhao, Z.; Newton, R. C.; Leister, W. H.; Strauss, K. A. Tertahedron Lett. 2002, 43, 4467-4470.
9. (c) Kamal, A.; Ramesh, G.; Laxman, N. Synth. Commun. 2001, 31, 827-833.
10. (d) Shimizu, T.; Ohzeki, T.; Hiramoto, K.; Hori, N.; Nakata, T. Synthesis 1999, 1373-1385.
11. (e) Kumar Sampath, H. M.; Subba Reddy, B. V.; Aujaneyulu, S.; Yadav, J. S. Tetrahedron Lett. 1998, 39, 7385-7388.
12. (a) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42, 3131-3133.
13. (b) Sridhar, P. R.; Prabhu, K. R.; Chaudrasekaran, S. J. Org. Chem. 2003, 68, 5261-5264.
14. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796-2797.
15. (d) Goulaonic-Dubois, C.; Hesse, M. Tetrahedron Lett. 1995, 36, 7427-7430.
16. (e) Capperucci, A.; Degli'Innocenti, A.; Fumicello, M.; Mauriello, G.; Scafato, P.; Spagnolo, P. J. Org. Chem. 1995, 60, 2254-2256.
17. (f) Samano, M. C.; Robius, M. J. Tetrahedron Lett. 1991, 32, 6293-6296.
18. (g) Rolla, F. J. Org. Chem. 1982, 47, 4327-4329.
19. (h) Kondo, T.; Nakai, H.; Goto, T. Tetrahedron 1973, 29, 1801-1806.
20. (i) Corey, E. J.; Nicolaou, K. C.; Balanson, R. D.; Machide, Y. Synthesis 1975, 590-591.
21. (a) Pal, B.; Jaisankar, P.; Giri, V. S. Synth. Commun. 2004, 34, 1317-1323.
22. (a) Kraus, T.; Budesinsky, T.; Cisarova, I.; Zavada, J. Eur. J. Org. Chem. 2004, 4060-4069.
23. (b) Kusumoto, S.; Sakai, K.; Shiba, T. Bull. Soc. Chim. Jpn. 1986, 59, 1296-1298.
24. Shaw, S. J.; Abbanat, D.; Ashley, G. W.; Bush, K.; Foleno, B.; Macielag, M.; Zhang, D.; Myles, D. C. J. Antibiot. 2005, 58, 167-177.
25. Borzilleri, R. M.; Zheng, X.; Schmidt, R. J.; Johnson, J. A.; Kim, S.-H.; DiMarco, J. D.; Fairchild, C. R.; Gougoutas, J. Z.; Lee, F. Y. F.; Long, B. H.; Vite, G. D. J. Am. Chem. Soc. 2000, 122, 8890-8897.
26. Balicki, R. Chem. Ber. 1990, 123, 647-648.
27. (a) Kamal, A.; Prasad, B. R.; Ramana, A. V.; Babu, A. H.; Reddy, K. S. Tetrahedron Lett. 2004, 45, 3507-3509.
28. (b) Kamal, A.; Ramana, K. V.; Aukati, H. B.; Ramana, A. V. Tetrahedron Lett. 2002, 43, 6861-6863.
29. Pathak, D.; Laskar, D. D.; Prajapath, D.; Sandthu, J. S. Chem. Lett. 2000, 816-917.
30. (a) Duan, Z.; Xuan, X.; Wu, Y. Tetrahedron Lett. 2007, 48, 5157-5159.
31. (b) Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006, 8, 19-22.
32. (c) Bolm, C.; Legras, J.; La Pain, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254.
33. (d) Christoffers, J. Synlett 2001, 723-732.
34. (e) Barrett, I. C.; Kerr, M. A. Synlett 2000, 1673-1675.
35. Allen, D. M.; Ler, L. T. J. Environ. Monit. 1999, 1, 103-108.
36. (a) Blackmond, D. G.; Armostrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798-3800.
37. (b) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford 1998.
38. (a) Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
39. (b) Trost, B. M. Science 1991, 254, 1471-1477.
40. Sabitha, G.; Yadav, J. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley-VCH: Weinheim, 2006.
41. 3, in fact, shows the same toxicity level as sodium chloride (Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: New York 1994).
42. (a) Bartoli, G.; Fernández-Bolaños, J. G.; Di Antonio, G.; Foglia, G.; Giuli, S.; Gunnella, R.; Mancinelli, M.; Marcantoni, E.; Paoletti, M. J. Org. Chem. 2007, 72, 6029-6036 and references cited therein.
43. (b) Bartoli, G.; Giovannini, R.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Melchiorre, P.; Paoletti, M.; Sambri, L. Eur. J. Org. Chem. 2006, 1476-1482.
44. (c) Bartoli, G.; Marcantoni, E.; Sambri, L. Synlett 2003, 2101-2116.
45. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
46. Niimi, K.-J.; Serita, S.; Hiraoka, T.; Yokozawa, T. Tetrahedron Lett. 2000, 41, 7075-7078.
47. Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5775-5776.
48. For reviews in microwave-assisted area, see: (a) Larhed, M.; Olofssson, K. Microwave Methods in Organic Synthesis; Springer: Berlin, 2006:
49. (b) Tierney, J. P.; Lindström, P. Microwave-Assisted Organic Synthesis; Blackwell Publishing: Oxford, 2005.
50. (c) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
51. (a) Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2005, 70, 1941-1944.
52. (b) Bartoli, G.; Bartolacci, M.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Torregiani, E. J. Org. Chem. 2004, 69, 169-174.
53. (c) Bartoli, G.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L. Synthesis 2004, 895-900.
54. (d) Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 68, 4594-4597.
55. Although multiple methods for the preparation of organic azides for different purposes are known (Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599),
56. we prefer Kotsuki's procedure by conversion of alcohols to corresponding sulfonates and subsequent nucleophilic substitution by azide anion (Kotsuki, H.; Araki, T.; Miyazaki, A.; Iwasaki, M.; Dana, P. K. Org. Lett. 1999, 3, 499-502).
57. This methodology does not use dichlofomethane as solvent, and then it avoids the presence of an explosive byproduct, the bis-azidomethane, that it could form by reaction of dichloromethane with the nucleophilic azide. See: Hassner, A.; Stern, M.; Gottlieb, H.; Frolow, F. J. Org. Chem. 1990, 55, 2304-2306.
58. Mixing pure liquids without solvents to dissipate any exothermic decomposition of the reagents or products may be dangerous on a large scale.
59. Bartoli, G.; Cupone, G.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Marcantoni, E.; Procopio, A. Synlett 2001, 1897-1900.
60. Mc Manus, M. J.; Berchtold, G. A.; Jerina, D. M. J. Am. Chem. Soc. 1985, 107, 2977-2978.
61. Shimizu, T.; Ohzeki, T.; Hiramoto, K.; Hori, N.; Nakata, T. Synthesis 1999, 1373-1385.
62. The chiral amine 21 was hypothesized to be (1S,2S, 5R)-configurated as reported in the literature (Smith, H. E.; Gordon, A. W.; Bridges, A. F. J. Org. Chem. 1974, 39, 2309-2311).
63. Crotti, P.; Dell'Omodarme, G.; Ferretti, M.; Macchia, F. J. Am. Chem. Soc. 1987, 109, 1463-1469.
64. Di Deo, M.; Marcantoni, E.; Torregiani, E.; Bartoli, G.; Bellucci, M. C.; Bosco, M.; Sambri, L. J. Org. Chem. 2000, 65, 2830-2833.
65. Crotti, P.; Chini, M.; Uccello-Barretta, G.; Macchia, F. J. Org. Chem. 1989, 54, 4525-4529.
66. Hoffmann, R. V.; Kim, H.-O. Tetrahedron Lett. 1990, 31, 2953-2956.
67. Hoffmann, R. V.; Kim, H.-O. Tetrahedron 1992, 48, 3007-3020.
68. (a) Liu, C.-Y.; Knochel, P. J. Org. Chem. 2007, 72, 7106-7115.
69. (b) Rao, H. S. P. Synth. Commun. 1994, 24, 549-555.
70. Zhu, W.; Ma, D. Chem. Commun. 2004, 888-889.
71. Pinney, K. G.; Katzenellenbogen, J. A. J. Org. Chem. 1991, 56, 3125-3133.
72. (a) Razzaq, T.; Kappe, C. O. Tetrahedron Lett. 2007, 48, 2513-2517.
73. (b) Smith, C. J.; Iglesias-Sigüenza, F. J.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 2758-2761.
74. (c) Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141-1150.
75. (d) Hesse, S.; Perspicace, E.; Kirsch, G. Tetrahedron Lett. 2007, 48, 5261-5264.
76. Microwave irradiation experiments were conducted using a CEM Discover monomode reactor with the temperature monitored by a built-in infrared sensor. This reactor is equipped with PowerMax technology that allows simultaneous cooling of a reaction with compressed gas while irradiating it with microwave energy (enhanced microwave synthesis). Thus, energy can be continuously applied while keeping the bulk temperature at a set level: this feature prevents unwanted side reactions and allows for cleaner and faster reactions. For details, see http://www.cemsynthesis.
77. (a) Jia, C.-S.; Dong, Y.-W.; Tu, S.-J.; Wang, G.-W. Tetrahedron 2007, 63, 892-897.
78. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S. K.; Sabitha, R. G. Synlett 2001, 1134-1136.
79. Lee, J. W.; Jun, S. I.; Kim, K. Tetrahedron Lett. 2001, 42, 2709-2711.
80. Imamoto, T.; Takeda, N. Org. Synth. 1998, 76, 228-238.
81. Boyer, J. H.; Canter, F. C.; Hamer, J.; Putney, R. K. J. Am. Chem. Soc. 1956, 78, 325-327.
82. (a) Bartoli, G.; Bosco, M.; Giuliani, A.; Marcantoni, E.; Palmieri, A.; Petrini, M.; Sambri, L. J. Org. Chem. 2004, 69, 1290-1297.
83. (b) Marotta, E.; Foresti, E.; Marcelli, T.; Peri, F.; Righi, P.; Scardovi, N.; Rosini, G. Org. Lett. 2002, 4, 4451-4453.
84. The use of less than 5 equiv of NaI decreases not only the amount of the conversion but also the rate of the reaction.
85. +≡ N; see: The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: London, 1971; p 4.
86. Derivatives of polivalent iodine are highly unstable and can exist only as short lived reactive intermediate; see: Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
87. In this reaction, iodide ion is viewed as a Lewis base, and the iodine is a Lewis acid. Our solution appears yellow at the beginning then becomes brown for higher concentration of triiodide ion, and significant amount of triiodide has also been observed by mass spectral data.
88. Bartoli, G.; Giuliani, A.; Marcantoni, E.; Massaccesi, M.; Melchiorre, P.; Lanari, S.; Sambri, L. Adv. Synth. Catal. 2005, 347, 1673-1680.
89. Janzen, E. G.; Wilcox, A. L.; Manoharant, V. J. Org. Chem. 1993, 58, 3597-3599.
90. Hwu, J. R.; Jain, M. L.; Tsai, F.-Y.; Tsay, S.-C.; Balakumar, A.; Hakimelahi, G. H. J. Org. Chem. 2000, 65, 5077-5084.
91. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W.-L. Chem. Rev. 2002, 102, 2227-2302.
92. Lawrence, S. A. Amines: Synthesis, Properties, and Applications; Cambridge University Press: Cambridge 2004.
93. Presented in this Experimental Section is the general procedure for this transformation, complete experimental procedures, and spectral data for new compounds.
94. For TLC detection of azide starting materials we have used Seebach staining solution, which is a mixture of molibdate phosphoric acid, cerium-(IV) sulfate tetrahydrate, sulfuric acid, and water.