Metal catalyst, method of c-n coupling using the same and applications of the same

Abstract

The present disclosure relates to a metal catalyst for C—H bond activation and/or C—N coupling reaction, and a method using the same and application thereof. Specifically, a metal catalyst represented by the following formula: wherein Q is a 5 or 6 membered aromatic ring; W, X, and Y are the same or different, and are independently N, S, P, or O; M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; Z is halide (F, Cl, Br, or I), acetate, water, or hydroxyl; R 1 and R 2 are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl.

What is claimed is: 
     
         1 . A metal catalyst represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein 
         Q is a 5 or 6 membered aromatic ring; 
         W, X, and Y are the same or different, and are independently N, S, P, or O; 
         M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; 
         Z is halide (F, Cl, Br, or I), acetate, water, or hydroxyl; 
         R 1  and R 2  are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl. 
       
     
     
         2 . The metal catalyst according to  claim 1  represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein 
         W, X, and Y are the same or different, and are independently N, S, P, or O; 
         M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; 
         Z is halide (F, Cl, Br, or I), acetate, water, or hydroxyl; 
         R 1  and R 2  are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl. 
       
     
     
         3 . The metal catalyst according to  claim 1  represented by the following formula: 
       
         
           
           
               
               
           
         
         wherein 
         W, X, and Y are the same or different, and are independently N, S, or P; 
         M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; 
         Z is halide (F, Cl, Br, or I), acetate, water, or hydroxyl; 
         R 1  and R 2  are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl. 
       
     
     
         4 . The metal catalyst according to  claim 1 , wherein W, X, and Y are the same. 
     
     
         5 . The metal catalyst according to  claim 1 , wherein M is Ni, Pd, Fe, Co, Cr, Mn, Cu, or Pt. 
     
     
         6 . A method for C—H bond activation and/or C—N coupling reaction comprising using the metal catalyst according to  claim 1 . 
     
     
         7 . The method according to  claim 6 , wherein the C—N coupling reaction forms C—N bonds between a sp 3  carbon and a primary or secondary amine to form substituted or an alkylated amine. 
     
     
         8 . The method according to  claim 7 , wherein the primary or secondary amine is an aliphatic or aromatic amine. 
     
     
         9 . The method according to  claim 7 , wherein sp 3  carbon is an aliphatic and aromatic hydrocarbon. 
     
     
         10 . The method according to  claim 6 , wherein the C—H bond activation and/or C—N coupling reaction is performed under ambient and mild conditions. 
     
     
         11 . The method according to  claim 6 , wherein the C—H bond activation and/or C—N coupling reaction is performed without the presence of an oxidant or a base. 
     
     
         12 . The method according to  claim 6 , wherein the C—N coupling reaction forms C—N bonds between aliphatic amines, to form a cyclic amine. 
     
     
         13 . The method according to  claim 6 , wherein the C—N coupling reaction forms C—N bonds between primary amines, to obtain an oligomeric compound. 
     
     
         14 . The method according to  claim 6 , wherein the C—H bond activation and/or C—N coupling reaction is performed in presence of an oxidant or a base. 
     
     
         15 . The method according to  claim 14 , the C—H bond activation and/or C—N coupling reaction is performed in presence of an oxidant that is selected from a group consisting of oxygen, hydrogen peroxide, t-butylhydroperoxide, peracetic acid, m-chloroperbenzoic acid, iodosylbenzene, phenyliododiacetate, iodine, sodium perborate, sodium hypochlorite, sodium persulfate, potassium persulfate, pyridine N-oxide, dibromoethane, manganese dioxide, cerium oxide, and sodium percarbonate. 
     
     
         16 . The method according to  claim 14 , the C—H bond activation and/or C—N coupling reaction is performed in presence of a base that is selected from a group consisting of sodium, potassium, or calcium base of carbonate, tert-butoxide, and hydride. 
     
     
         17 . The method according to  claim 6 , wherein the amount of the metal catalyst is 0.02 to 2 mol %.