Catalysed ligation of azides and acetylenes

Abstract

A copper catalyzed click chemistry ligation process is employed to bind azides and terminal acetylenes to provide 1,4-disubstituted 1,2,3-triazole triazoles. The process comprises contacting a solution of an organic azide and a terminal alkyne with a source of catalytic Ru ion to form a 1,4-disubstituted 1,2,3-triazole.

What is claimed is: 
     
         1 . A copper catalyzed process for preparing a 1,4-disubstituted 1,2,3-triazole comprising:
 contacting a solution of an organic azide and a terminal alkyne with a catalytic metal salt to form a 1,4-disubstituted 1,2,3-triazole, wherein the catalytic metal salt comprises a ruthenium (Ru) ion.   
     
     
         2 . The process of  claim 1 , wherein the solution further comprises a reducing agent for reducing the Ru ion to a catalytically active form. 
     
     
         3 . The process of  claim 2 , wherein the reducing agent comprises one or more material selected from ascorbate, hydroquinone, glutathione, and cysteine. 
     
     
         4 . The process of  claim 2 , wherein the reducing agent comprises an applied electric potential. 
     
     
         5 . The process of  claim 2 , wherein the reducing agent comprises one or more metal selected from the group consisting of Al, Be, Co, Cr, Fe, Mg, Mn, Ni, and Zn. 
     
     
         6 . The process of  claim 2 , wherein the solution comprises at least one solvent selected from the group consisting of water, a nitrile, and an alcohol. 
     
     
         7 . The process of  claim 2 , wherein the solution comprises at least one solvent selected from the group consisting of acetonitrile, ethanol, and tert-butanol. 
     
     
         8 . The process of  claim 2 , wherein the solution is an aqueous solution. 
     
     
         9 . The process of  claim 1 , wherein the solution comprises at least one solvent selected from the group consisting of water, a nitrile, and an alcohol. 
     
     
         10 . The process of  claim 1 , wherein the solution comprises at least one solvent selected from the group consisting of acetonitrile, ethanol, and tert-butanol. 
     
     
         11 . The process of  claim 1 , wherein the solution is an aqueous solution.