One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3897-3899

  Feldman, Alina K ^a   Colasson, Benoît ^a   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; MOLECULAR WEIGHT; SOLUBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALKYNES; AZIDES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; TRIAZOLES; VINYL COMPOUNDS;

EID: 8744304751     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048859z     Document Type: Article

References (12)

1. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
2. (b) Tornœ, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
3. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
4. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
5. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
6. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
7. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
8. For recent examples of the azide - acetylene ligation reaction, please see: (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192. (b) Speers, A. E.; Adam, G. C.; Gravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686. (c) Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782. (d) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164. (e) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051. (f) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932.
9. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 2, 351.
10. To the best of our knowledge, there is only one report describing an in situ formation of 1,2,3-triazoles from alkyl halides, alkynes, and sodium azide. This method requires heating the reagents at high temperatures for extended periods of time, resulting in a mixture of both regioisomers, and gives low yields. Maksikova, A. V.; Serebryakova, E. S.; Tikhonova, L. G.; Vereshagin, L. I. Chem. Heterocycl. Comp. 1980, 1284.
11. Zhu, W.; Ma, D. Chem. Commun. 2004, 7, 888.
12. 4, and evaporated to yield 3p as a pale yellow oil (112 mg, 94%).