Efficient One-Pot Synthesis of 1-Aryl 1,2,3-Triazoles from Aryl Halides and Terminal Alkynes in the Presence of Sodium Azide

Jacob Andersen; Simon Bolvig; Xifu Liang

doi:10.1055/s-2005-921887

LETTER

Efficient One-Pot Synthesis of 1-Aryl 1,2,3-Triazoles from Aryl Halides and Terminal Alkynes in the Presence of Sodium Azide

Jacob Andersen^a, Simon Bolvig^b, Xifu Liang*^a
^a Department of Medicinal Chemistry, LEO Pharma, Industriparken 55, 2750 Ballerup, Denmark
Fax: +45(7226)3320; e-Mail: xifu.liang@leo-pharma.com;
^b Department of Spectroscopy and Physical Chemistry, LEO Pharma, Industriparken 55, 2750 Ballerup, Denmark

Abstract

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Abstract

An efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl bromides/iodides and terminal alkynes in the presence of sodium azide is described. In the case of aryl iodides, the reactions proceeded at room temperature. The reactions normally gave high yields.

Key words

1,2,3-triazoles - one-pot - copper - 1,3-dipolar cycloaddition - catalyst

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References

1 Katritzky AR. Zhang Y. Singh SK. Heterocycles 2003, 60: 1225

2a Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

2b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

3 Kolb HC. Sharpless KB. Drug Discov. Today 2003, 8: 1128 ; and reference cited therein

4a Wu P. Feldman AK. Nugent AK. Hawker CJ. Scheel A. Voit B. Pyun J. Frechet JMJ. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2004, 43: 3928

4b Helms B. Mynar JL. Hawker CJ. Frechet JMJ. J. Am. Chem. Soc. 2004, 126: 15020

4c Scheel A. Komber H. Voit B. Macromol. Rapid Commun. 2004, 25: 1175

4d Parent M. Mongin O. Kamada K. Katan C. Blanchard-Desce M. Chem. Commun. 2005, 2029

4e van Steenis DJVC. David ORP. van Strijdonck GPF. van Maarseveen JH. Reek JNH. Chem. Commun. 2005, 4333

5a Löber S. Rodriguez-Loaiza P. Gmeiner P. Org. Lett. 2003, 5: 1753

5b Harju K. Vahermo M. Mutikainen I. Yli-Kauhaluoma J. J. Comb. Chem. 2003, 5: 826

5c Khanetskyy B. Dallinger D. Kappe CO. J. Comb. Chem. 2004, 6: 884

5d Tornoe CW. Sanderson SJ. Mottram JC. Coombs GH. Meldal M. J. Comb. Chem. 2004, 6: 312

6a Blass BE. Coburn KR. Faulkner AL. Seibel WL. Srivastava A. Tetrahedron Lett. 2003, 44: 2153

6b Feldman AK. Colasson B. Fokin VV. Org. Lett. 2004, 6: 3897

6c Appukkuttan P. Dehaen W. Fokin VV. Van der Eycken E. Org. Lett. 2004, 6: 4223

6d Kacprzak K. Synlett 2004, 943

6e Chittaboina S. Xie F. Wang Q. Tetrahedron Lett. 2005, 46: 2331

7 Zhu W. Ma D. Chem. Commun. 2004, 888

8 Andersen J. Madsen U. Björkling F. Liang X. Synlett 2005, 2209

9 Wang Q. Chan TR. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc. 2003, 125: 3192

10 Biling JF. Nilsson UJ. J. Org. Chem. 2005, 70: 4847

11 Sharpless KB, Fokin V, Rostovtsev V, Green L, and Himo F. inventors; PCT Int. Appl. WO200310172.

12 The steric effect was also observed by others. For examples, see: Deng W. Liu L. Zhang C. Liu M. Guo Q.-X. Tetrahedron Lett. 2005, 46: 7295

13 For a Cu(I)-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles, see: Jin T. Kamijo S. Yamamoto Y. Eur. J. Org. Chem. 2004, 3789