Simple conversion of aromatic amines into azides

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2571-2572

  Liu, Qi ^a   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; AZIDE;

ARTICLE; CHEMICAL MODEL; SYNTHESIS;

AMINES; AZIDES;

EID: 0141742606     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034919+     Document Type: Article

References (27)

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2. For reviews on aryl azides as photoaffinity labels and references therein, see: (a) Bayley, H.; Staros, J. V. In Azides and Nitrenes, Scriven, E. F. V., Ed.; Academic Press: Orlando, 1984; pp 433-490. (b) Annals of the New York Academy of Sciences; Tometsko, A. M., Richards, F. M., Eds.; New York Academy of Sciences, New York, 1980; Applications of Photochemistry in Probing Biological Targets, Vol. 346. (c) Radominska, A.; Drake, R. R. Methods Enzymol. 1994, 230, 330-339. (d) Fedan, J. S.; Hogaboom, G. K.; O'Donnell, J. P. Biochem. Pharmacol. 1984, 33, 1167-1180.
3. For reviews on aryl azides as photoaffinity labels and references therein, see: (a) Bayley, H.; Staros, J. V. In Azides and Nitrenes, Scriven, E. F. V., Ed.; Academic Press: Orlando, 1984; pp 433-490. (b) Annals of the New York Academy of Sciences; Tometsko, A. M., Richards, F. M., Eds.; New York Academy of Sciences, New York, 1980; Applications of Photochemistry in Probing Biological Targets, Vol. 346. (c) Radominska, A.; Drake, R. R. Methods Enzymol. 1994, 230, 330-339. (d) Fedan, J. S.; Hogaboom, G. K.; O'Donnell, J. P. Biochem. Pharmacol. 1984, 33, 1167-1180.
4. For reviews on aryl azides as photoaffinity labels and references therein, see: (a) Bayley, H.; Staros, J. V. In Azides and Nitrenes, Scriven, E. F. V., Ed.; Academic Press: Orlando, 1984; pp 433-490. (b) Annals of the New York Academy of Sciences; Tometsko, A. M., Richards, F. M., Eds.; New York Academy of Sciences, New York, 1980; Applications of Photochemistry in Probing Biological Targets, Vol. 346. (c) Radominska, A.; Drake, R. R. Methods Enzymol. 1994, 230, 330-339. (d) Fedan, J. S.; Hogaboom, G. K.; O'Donnell, J. P. Biochem. Pharmacol. 1984, 33, 1167-1180.
5. For reviews on aryl azides as photoaffinity labels and references therein, see: (a) Bayley, H.; Staros, J. V. In Azides and Nitrenes, Scriven, E. F. V., Ed.; Academic Press: Orlando, 1984; pp 433-490. (b) Annals of the New York Academy of Sciences; Tometsko, A. M., Richards, F. M., Eds.; New York Academy of Sciences, New York, 1980; Applications of Photochemistry in Probing Biological Targets, Vol. 346. (c) Radominska, A.; Drake, R. R. Methods Enzymol. 1994, 230, 330-339. (d) Fedan, J. S.; Hogaboom, G. K.; O'Donnell, J. P. Biochem. Pharmacol. 1984, 33, 1167-1180.
6. For a review, see: (a) Biffin, M. E. C.; Miller, J.; Paul, D. B. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971; pp 147-176. See also: (b) Kauer, J. C.; Carboni, R. A. J. Am. Chem. Soc. 1967, 89, 2633-2637. (c) Takahashi, M.; Suga, D. Synthesis 1998, 7, 986-990.
7. For a review, see: (a) Biffin, M. E. C.; Miller, J.; Paul, D. B. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971; pp 147-176. See also: (b) Kauer, J. C.; Carboni, R. A. J. Am. Chem. Soc. 1967, 89, 2633-2637. (c) Takahashi, M.; Suga, D. Synthesis 1998, 7, 986-990.
8. For a review, see: (a) Biffin, M. E. C.; Miller, J.; Paul, D. B. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971; pp 147-176. See also: (b) Kauer, J. C.; Carboni, R. A. J. Am. Chem. Soc. 1967, 89, 2633-2637. (c) Takahashi, M.; Suga, D. Synthesis 1998, 7, 986-990.
9. See for example: (a) Smith, P. A. S.; Rowe, C. D.; Bruner, L. B. J. Org. Chem. 1969, 34, 3430-3433. (b) Smith, P. A. S.; Budde, G. F.; Chou, S.-S. P. J. Org. Chem. 1985, 50, 2062-2064. (c) Gavenonis, J.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 8536-8537. (d) Gavenonis, J.; Tilley, T. D. Organometallics 2002, 21, 5549-5563.
10. See for example: (a) Smith, P. A. S.; Rowe, C. D.; Bruner, L. B. J. Org. Chem. 1969, 34, 3430-3433. (b) Smith, P. A. S.; Budde, G. F.; Chou, S.-S. P. J. Org. Chem. 1985, 50, 2062-2064. (c) Gavenonis, J.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 8536-8537. (d) Gavenonis, J.; Tilley, T. D. Organometallics 2002, 21, 5549-5563.
11. See for example: (a) Smith, P. A. S.; Rowe, C. D.; Bruner, L. B. J. Org. Chem. 1969, 34, 3430-3433. (b) Smith, P. A. S.; Budde, G. F.; Chou, S.-S. P. J. Org. Chem. 1985, 50, 2062-2064. (c) Gavenonis, J.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 8536-8537. (d) Gavenonis, J.; Tilley, T. D. Organometallics 2002, 21, 5549-5563.
12. See for example: (a) Smith, P. A. S.; Rowe, C. D.; Bruner, L. B. J. Org. Chem. 1969, 34, 3430-3433. (b) Smith, P. A. S.; Budde, G. F.; Chou, S.-S. P. J. Org. Chem. 1985, 50, 2062-2064. (c) Gavenonis, J.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 8536-8537. (d) Gavenonis, J.; Tilley, T. D. Organometallics 2002, 21, 5549-5563.
13. (a) Fisher, W.; Anselme, J.-P. J. Am. Chem. Soc. 1967, 89, 5284-5285.
14. (b) Nielsen, P. E. Tetrahedron Lett. 1979, 20, 2705-2706.
15. Sandler, S.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1971; pp 268-284.
16. For early examples, see: (a) Ruff, J. K. Inorg. Chem. 1965, 4, 567-570. (b) Caveander, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. (c) Zaloom, J. R.; David C. J. Org. Chem. 1981, 46, 5173-5176. (d) Eaton, P. E.; Fisher, A. M.; Hormann, R. E. Synlett 1990, 737-738.
17. For early examples, see: (a) Ruff, J. K. Inorg. Chem. 1965, 4, 567-570. (b) Caveander, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. (c) Zaloom, J. R.; David C. J. Org. Chem. 1981, 46, 5173-5176. (d) Eaton, P. E.; Fisher, A. M.; Hormann, R. E. Synlett 1990, 737-738.
18. For early examples, see: (a) Ruff, J. K. Inorg. Chem. 1965, 4, 567-570. (b) Caveander, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. (c) Zaloom, J. R.; David C. J. Org. Chem. 1981, 46, 5173-5176. (d) Eaton, P. E.; Fisher, A. M.; Hormann, R. E. Synlett 1990, 737-738.
19. For early examples, see: (a) Ruff, J. K. Inorg. Chem. 1965, 4, 567-570. (b) Caveander, C. J.; Shiner, V. J. J. Org. Chem. 1972, 37, 3567-3569. (c) Zaloom, J. R.; David C. J. Org. Chem. 1981, 46, 5173-5176. (d) Eaton, P. E.; Fisher, A. M.; Hormann, R. E. Synlett 1990, 737-738.
20. Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
21. See, for example: (a) Ding, Y.; Swayze, E. E.; Hofstadler, S. A.; Griffey, R. H. Tetrahedron Lett. 2000, 41, 4049-4052. (b) Greenberg, W. A.; Priestley, E. S.; Sears, P. S.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527-6541.
22. See, for example: (a) Ding, Y.; Swayze, E. E.; Hofstadler, S. A.; Griffey, R. H. Tetrahedron Lett. 2000, 41, 4049-4052. (b) Greenberg, W. A.; Priestley, E. S.; Sears, P. S.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527-6541.
23. 3 (10 mL) and used immediately.
24. Although we have not experienced any difficulties in handling tryflyl azide, care should be taken due to the potentially explosive nature of such compounds (see ref 7b).
25. +.
26. Mechanism for the metal-catalyzed diazo transfer for the aliphatic amine-to-azide interconversion has been proposed by Wong. See: Nyffeler, P. T.; Liang, C. H.; Koeller, K. M.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 10773-10778.
27. Attempts to push the reaction at elevated temperatures have not resulted in any improvement, possibly due to the concomitant decomposition of 1.