CuI/Et₂NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Abstract

A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

Keywords

green solvent - glycerol - copper(I) iodide - diethylamine - triazoles - one-pot synthesis

• References


For selected examples:
• 1a Horne WS. Yadav MK. Stout CD. Ghadiri MR. J. Am. Chem. Soc. 2004; 126: 15366
• 1b Pagliai F. Pirali T. Grosso ED. Brisco RD. Tron GC. Sorba G. Genaz-zani AA. J. Med. Chem. 2006; 49: 467
• 1c Angell YL. Burgess K. Chem. Soc. Rev. 2007; 36: 1674
• 1d Meldal M. Tornoe CW. Chem. Rev. 2008; 108: 2952
• 2a Bock VD. Speijer D. Hiemstra H. van Maarseveen JH. Org. Biomol. Chem. 2007; 5: 971
• 2b Dedola S. Nepogodiev SA. Field RA. Org. Biomol. Chem. 2007; 5: 1006

For selected examples:
• 3a Wu P. Feldman AK. Nugent AK. Hawker CJ. Scheel A. Voit B. Pyun J. Fréchet JM. J. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2004; 43: 3928
• 3b Nandivada H. Jiang XW. Lahann J. Adv. Mater. 2007; 19: 2197
• 3c Johnson TC. Totty WG. Wills M. Org. Lett. 2012; 14: 5230

For selected examples:
• 4a Kolb HC. Sharpless KB. Drug. Discov. Today 2003; 8: 1128
• 4b Sugawara A. Sunazuka T. Hirose T. Nagai K. Yamaguchi Y. Hanaki H. Sharpless KB. Omura S. Bioorg. Med. Chem. Lett. 2007; 17: 6340
• 4c Tron GC. Pirali T. Billington RA. Canonico PL. Sorba G. Genazzani AA. Med. Res. Rev. 2008; 28: 278

For selected examples, see ref. 1d and:
• 5a Dai Q. Gao W. Liu D. Kapzes LM. Zhang X. J. Org. Chem. 2006; 71: 3928
• 5b Liu YX. Yan WM. Chen YF. Petersen JL. Shi XD. Org. Lett. 2008; 10: 5389

For selected examples:
• 6a Meldal M. Christensen CC. Tornøe W. J. Org. Chem. 2002; 67: 3057
• 6b Li Z. Seo TS. Ju J. Tetrahedron Lett. 2004; 45: 3143
• 6c Zhang L. Chen X. Xue P. Sun HH. Y. Williams ID. Sharpless KB. Fokin VV. Jia G. J. Am. Chem. Soc. 2005; 127: 15998
• 6d Golas PL. Tsarevsky NV. Sumerlin BS. Matyjaszewski K. Macromolecules. 2006; 39: 6451
• 6e Kwok SW. Fotsing JR. Fraser RJ. Rodionov VO. Fokin VV. Org. Lett. 2010; 12: 4217

For selected examples, see ref. 1d and:
• 7a Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
• 7b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 7c Rodionov VO. Fokin VV. Finn MG. Angew. Chem. Int. Ed. 2005; 44: 2210
• 7d Debets MF. van Berkel SS. Dommerholt J. Dirks AJ. Rutjes FP. J. T. van Delft FL. Acc. Chem. Res. 2011; 44: 805
• 8 Scriven EF. V. Turnbull K. Chem. Rev. 1988; 88: 297

For selected examples:
• 9a Feldman AK. Colasson B. Fokin VV. Org. Lett. 2004; 6: 3897
• 9b Baig RB. N. Varma RS. Chem. Commun. 2012; 48: 5853
• 9c Mukherjee N. Ahammed S. Bhadra S. Ranu BC. Green Chem. 2013; 15: 389
• 9d Wei F. Li H. Song C. Ma Y. Zhou L. Tung C. Xu Z. Org. Lett. 2015;  17: 2860

For selected examples:
• 10a Liu PN. Siyang HX. Zhang L. San Tse SK. Jia G. J. Org. Chem. 2012; 77: 5844
• 10b Ali A. Correa AG. Alves D. Zukerman-Schpector J. Westermann B. Ferreira MA. B. Paixao MW. Chem. Commun. 2014; 50: 11926
• 10c Shil AK. Kumar S. Sharma S. Chaudhary A. Das P. RSC Adv. 2015; 5: 11506
• 11 Capello C. Fisher U. Kungerbühler K. Green Chem. 2007; 9: 927
• 12 Radatz CS. Soares LA. Vieira ER. Alves D. Russowsky D. Schneider PH. New J. Chem. 2014; 38: 1410
• 13 Tasca E. Sorella G. Sperni L. Strukul G. Scarso A. Green Chem. 2015; 17: 1414
• 14 Alonso F. Moglie Y. Radivoy G. Yus M. J. Org. Chem. 2011; 76: 8394

For selected examples:
• 15a DeSimone JM. Science 2002; 297: 799
• 15b Nelson WM. Green Solvents for Chemistry: Perspectives and Practice . Oxford University Press; New York: 2003
• 15c Clark JH. Taverner SJ. Org. Process Res. Dev. 2007; 11: 149
• 16a Gu Y. Barrault J. Jérôme F. Adv. Synth. Catal. 2008; 350: 2007
• 16b Gu Y. De Sousa R. Frapper G. Bachmann C. Barrault J. Jéřome F. Green Chem. 2009; 11: 1968

For selected examples:
• 17a Li J. Wang D. Zhang Y. Li J. Chen B. Org. Lett. 2009; 11: 3024
• 17b Alonso F. Moglie Y. Radivoy G. Yus M. Org. Biomol. Chem. 2011; 9: 6385
• 17c Haldón E. Nicasio MC. Perez PJ. Org. Biomol. Chem. 2015; 13: 9528