Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2005(19): 2941-2947
DOI: 10.1055/s-2005-921887
DOI: 10.1055/s-2005-921887
LETTER
© Georg Thieme Verlag Stuttgart · New York
Efficient One-Pot Synthesis of 1-Aryl 1,2,3-Triazoles from Aryl Halides and Terminal Alkynes in the Presence of Sodium Azide
Further Information
Received
1 September 2005
Publication Date:
27 October 2005 (online)
Publication History
Publication Date:
27 October 2005 (online)
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
- 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, andHimo 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