Process for producing biaryl compound

Abstract

A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.

1 . A process for producing a biaryl compound, which comprises reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound,
 wherein the arylhydrazine compound is represented by the formula (1):
   Ar—NHN H 2    (1)
 
   
       wherein Ar represents a substituted or unsubstituted heteroaromatic group,
 the aryl compound is represented by the formula (2):
   Ar′  ( 2 )
 
 
 
       wherein Ar′ is a substituted or unsubstituted aromatic group and has at least one hydrogen atom bound to the aforementioned group, and
 the biaryl compound is represented by the formula (3):
   Ar—Ar′  (30
 
 
 
       wherein Ar and Ar′ are as defined above. 
     
     
         2 . The process according to  claim 1 , wherein the reaction is performed in the presence of at least one species selected from the group consisting of the following groups (A) and (B):
 (A) a Group Va element metal or a compound thereof, a Group Vla element metal or a compound thereof, a Group Vlla element metal or a compound thereof, and a Group Vllla element metal or a compound thereof,   (B) a Group Va element metal oxide, a Group Vla element metal oxide, a Group Vlla element metal oxide and a Group Vllla element metal oxide obtained by reacting the metal or the metal compound of the group (A) with hydrogen peroxide.   
     
     
         3 . The process for producing a biaryl compound according to  claim 1 , wherein hydrogen peroxide solution in water is used. 
     
     
         4 . The process for producing a biaryl compound according to  claim 1 , wherein the reaction is performed using hydrogen peroxide solution in water and in the presence of a phase transfer catalyst. 
     
     
         5 . The process for producing a biaryl compound according to  claim 4 , wherein the phase transfer catalyst is quaternary ammonium salt or amine N-oxide.