Synthesis of 1,4-Disubstituted
1,2,3-Triazoles by Use of Copper(I) and Amino Acids Ionic Liquid
Catalytic System

Jincan Yan; Lei Wang

doi:10.1055/s-0029-1217111

PAPER

Synthesis of 1,4-Disubstituted 1,2,3-Triazoles by Use of Copper(I) and Amino Acids Ionic Liquid Catalytic System

Jincan Yan^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;

Abstract

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Abstract

An efficient and green one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from aryl iodides and alkyl chlorides, sodium azide, and terminal alkynes catalyzed by copper(I) and amino acid ionic liquid (AAIL) in [BMIM]BF₄ was developed. The reactions proceeded smoothly to generate the corresponding products in high yields. In addition, CuI, AAIL, and [BMIM]BF₄ could be recovered for six consecutive trials without significant loss of activity.

Key words

click reaction - triazoles - ionic liquids - amino acid - copper

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References

For recent reviews, see:

<A NAME="RF16709SS-1A">1a</A> Kolb HC. Sharpless KB. Drug Discovery Today 2003, 8: 1128

<A NAME="RF16709SS-1B">1b</A> Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004

<A NAME="RF16709SS-2">2</A> Breinbauer R. Kohn M. ChemBioChem 2003, 4: 1147

<A NAME="RF16709SS-3A">3a</A> Huisgen R. Szeimies G. Moebius L. Chem. Ber. 1967, 100: 2494

<A NAME="RF16709SS-3B">3b</A> Huisgen R. In 1,3-Dipolar Cycloaddition Chemistry Padwa A. Wiley; New York: 1984. p.1-176

<A NAME="RF16709SS-3C">3c</A> Huisgen R. Pure Appl. Chem. 1989, 61: 613

<A NAME="RF16709SS-3D">3d</A> Gil MV. Arevalo MJ. Lopez O. Synthesis 2007, 1589

<A NAME="RF16709SS-4A">4a</A> Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

<A NAME="RF16709SS-4B">4b</A> Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

<A NAME="RF16709SS-5A">5a</A> Manetsch R. Krasinski A. Radic Z. Raushel J. Taylor P. Sharpless KB. Kolb HC. J. Am. Chem. Soc. 2004, 126: 12809

<A NAME="RF16709SS-5B">5b</A> Lewis WG. Green LG. Grynszpan F. Radic Z. Carlier PR. Taylor P. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 1053

<A NAME="RF16709SS-6">6</A> Speers AE. Adam GC. Cravatt BF. J. Am. Chem. Soc. 2003, 125: 4686

<A NAME="RF16709SS-7A">7a</A> Pachón LD. Maarseveen JH. Rothenberg G. Adv. Synth. Catal. 2005, 347: 811

<A NAME="RF16709SS-7B">7b</A> Orgueira HA. Fokas D. Isome Y. Chan PCM. Baldino CM. Tetrahedron Lett. 2005, 46: 2911

<A NAME="RF16709SS-8A">8a</A> Wu P. Alina KF. Anne KN. Craig JH. Scheel A. Voit B. Pyun J. Jean MJF. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2004, 43: 3928

<A NAME="RF16709SS-8B">8b</A> Binder WH. Kluger C. Macromolecules 2004, 37: 9321

<A NAME="RF16709SS-9">9</A> Mantovani G. Ladmiral V. Tao L. Haddleton DM. Chem. Commun. 2005, 2089

<A NAME="RF16709SS-10">10</A> Speers AE. Cravatt BF. Chem. Biol. 2004, 11: 535

<A NAME="RF16709SS-11A">11a</A> Link AJ. Tirrell DA. J. Am. Chem. Soc. 2003, 125: 11164

<A NAME="RF16709SS-11B">11b</A> Chan TR. Hilgraf R. Sharpless KB. Fokin VV. Org. Lett. 2004, 6: 2853

<A NAME="RF16709SS-12">12</A> Miao T. Wang L. Synthesis 2008, 363

<A NAME="RF16709SS-13">13</A> Li PH. Wang L. Lett. Org. Chem. 2007, 4: 23

<A NAME="RF16709SS-14">14</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

<A NAME="RF16709SS-15A">15a</A> Andersen J. Bolvig S. Liang XF. Synlett 2005, 2941

<A NAME="RF16709SS-15B">15b</A> Zhao YB. Yan ZY. Liang YM. Tetrahedron Lett. 2006, 47: 1545

<A NAME="RF16709SS-16">16</A> Ljungdahl N. Kann N. Angew. Chem. Int. Ed. 2009, 48: 642

<A NAME="RF16709SS-17">17</A> Reymond S. Cossy J. Chem. Rev. 2008, 108: 5359

<A NAME="RF16709SS-18">18</A> Falciola CA. Alexakis A. Eur. J. Org. Chem. 2008, 3765

<A NAME="RF16709SS-19">19</A> Stanley LM. Sibi MP. Chem. Rev. 2008, 108: 2887

<A NAME="RF16709SS-20A">20a</A> Ma D. Cai Q. Zhang H. Org. Lett. 2003, 5: 2453

<A NAME="RF16709SS-20B">20b</A> Ma D. Cai Q. Org. Lett. 2003, 5: 3799

<A NAME="RF16709SS-20C">20c</A> Zhu W. Ma D. J. Org. Chem. 2005, 70: 2696

<A NAME="RF16709SS-20D">20d</A> Xie X. Cai G. Ma D. Org. Lett. 2005, 7: 4693

<A NAME="RF16709SS-21">21</A> Ma D. Cai Q. Acc. Chem. Res. 2008, 41: 1450

<A NAME="RF16709SS-22A">22a</A> Welton T. Chem. Rev. 1999, 99: 2071

<A NAME="RF16709SS-22B">22b</A> Wasserscheid P. Welton T. Ionic Liquids in Synthesis Wiley-VCH; Weinheim: 2003.

<A NAME="RF16709SS-23">23</A> Ohno H. Fukumoto K. Acc. Chem. Res. 2007, 40: 1122

<A NAME="RF16709SS-24">24</A> Ranu BC. Banerjee S. Org. Lett. 2005, 7: 3049

<A NAME="RF16709SS-25">25</A> Appukkuttan P. Dehaen W. Fokin VV. Van der Eyken E. Org. Lett. 2004, 6: 4223

<A NAME="RF16709SS-26">26</A> Kacprzak K. Synlett 2005, 943

<A NAME="RF16709SS-27">27</A> Barral K. Moorhouse AD. Moses JE. Org. Lett. 2007, 9: 1809

<A NAME="RF16709SS-28">28</A> Wang ZX. Qin HL. Chem. Commun. 2003, 2450

<A NAME="RF16709SS-29">29</A> Tao CZ. Cui X. Li J. Liu AX. Liu L. Guo QX. Tetrahedron Lett. 2007, 48: 3525

<A NAME="RF16709SS-30">30</A> Moorhouse AD. Moses JE. Synlett 2008, 2089