Processes for the Preparation of Arylamine Compounds

Abstract

A process for the preparation of N-arylamine compounds, the process including: reacting a compound having an amino group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an N-arylamine compound; wherein the transition metal catalyst comprises a complex of a Group 8-10 metal and at least one chelating ligand comprising (R)—(—)-1-[(S)-2-dicyclohexylphosphino]-ferrocenyl]ethyldi-t-butylphosphine.

1 .- 15 . (canceled) 
     
     
         16 . A process for preparing a Group 15 atom and metal catalyst compound, the process comprising:
 a) preparing a ligand comprising an N-aryl amine compound by reacting a compound having an amino group with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an N-aryl amine compound, wherein the transition metal catalyst is formed by reacting a Group 8 metal catalyst precursor comprising palladium (II) acetate (Pd(OAc) 7 ) and at least one chelating ligand comprising (R)—(—)-1-[(S)-2-[dicyclohexylphosphino]-ferrocenyl]ethyldi-t-butylphosphine; and   b) combining the ligand prepared in step a) with a compound represented by the formula M n X n  where M is a Group 3 to 14 metal, n is the oxidation state of M, and X is an anionic group.   
     
     
         17 . The process of  claim 16 , wherein the compound having an amino group is selected from the group consisting of primary amines, secondary amines, and combinations thereof. 
     
     
         18 . The process of  claim 16 , wherein the compound having an amino group comprises at least one of diethylenetriamine, 1,5-diaminopentane, and 2,2′-oxydiethylamine. 
     
     
         19 . The process of  claim 16 , wherein the arylating compound comprises at least one compound having the formula: 
       
         
           
           
               
               
           
         
         wherein X is a halogen atom or a sulfur-containing leaving group, and R 1 , R 2 , R 3 , R 4 , R 5 are independently selected from the group consisting of H, CN, alkyl, alkoxy, vinyl, alkenyl, formyl, CF 3 , CCl 3 , halide, C 6 H 5 , amide, acyl, ester, alkoxy, amino, thioalkoxy, phosphino, and combinations thereof. 
       
     
     
         20 . The process of  claim 16 , wherein said arylating compound comprises at least one of 2,3,4,5,6-pentamethylbromobenzene and 2,4,6-trimethylbromobenzene. 
     
     
         21 . The process of  claim 16 , wherein the N-aryl amine compound comprises N 1 -(2,3,4,5,6-pentamethylphenyl)-N 2 -(2-(2,3,4,5,6-pentamethylpehenylamino)ethyl)ethane-1,2-diamine. 
     
     
         22 . The process of  claim 16 , further comprising combining the Group 15 containing metal catalyst compound with at least one of an activator and a support material. 
     
     
         23 . The process of  claim 16 , wherein the transition metal catalyst is present during the reacting at a concentration in the range from about 0.03 to about 1.0 mole percent, based on a total amount of the compound having an amino group, the arylating compound, and the transition metal catalyst. 
     
     
         24 . The process of  claim 16 , further comprising combining the N-aryl amine compound with a compound represented by the formula M n X n  where M is a Group 3 to 14 metal, n is the oxidation state of M, and X is an anionic group to form a Group 15 containing metal catalyst compound.