Coupling catalyst and process using the same

Abstract

There are disclosed a process for producing a coupling compound of formula (1): (Y-) n-1) R 1 -R 2 -(R 1 ) (n′-1)   (1), wherein R 1 and R 2 independently represent a substituted or unsubstituted aryl group, which process is characterized by reacting an unsaturated organic compound of formula (2): n′(R 1 X 1 n )   (2) wherein n, n′, and R 1 are the same as defined above, and X 1 is the same or different and independently represents a leaving group and bonded with a sp2 carbon atom of R 1 group, with a boron compound of formula (3): m{R 2 (BX 2 2 ) n′ }  (3) wherein R 2 and n′ are the same as defined above, X 2 represents a hydroxy group, an alkoxy group, in the presence of a catalyst containing (A) a nickel compound, and (B) a nitrogen-containing cyclic compound, and the catalyst.

1 - 18 . (canceled)  
   
   
       19 . A catalyst composition: 
 1) comprising (A) a nickel compound, (B) a nitrogen-containing cyclic compound selected from:    (a) a nitrogen-containing cyclic compound of formula (I):                          wherein Q represents    a substituted or unsubstituted alkylene group,    a substituted or unsubstituted alkenylene group,    a substituted or unsubstituted 1,2-phenylene group,    a substituted or unsubstituted 1,8-naphthylene group, or    —N═N— group,    R 10  represents    a substituted or unsubstituted hydrocarbon group, and    R 20  represents    a hydrogen atom, a substituted or unsubstituted hydrocarbon group,    alternatively, R 10  and R 20  are bonded at their terminals to form a substituted or unsubstituted alkylene, or alkenylene group,    (b) a substituted or unsubstituted pyridine or fused ring compound thereof of which conjugated acid has pKa of 5 or more,    (c) a substituted pyrimidine or substituted or unsubstituted fused pyrimidine compound of which conjugate acid has pKa of 3 or more,    (d) an enamine compound obtainable from a cyclic ketone compound and a cyclic secondary amine compound,    (e) a substituted or unsubstituted 2H-pyrrole, 3,4-dihydro-2H-pyrrole or 3H-pyrrole or fused ring compound thereof, or    (f) a substituted or unsubstituted N-hydrocarbyl 1,2,3-triazole, or a fused ring compound thereof, and    a solvent, provided that said solvent is not a solvent consisting of ethanol and 2,2-dimethoxypropane,    2) comprising (A) the nickel compound, (B) the nitrogen-containing cyclic compound as defined above, and a solvent consisting essentially of an aprotic organic solvent,    3) comprising (A1) a zero valent nickel compound, and (B) the nitrogen-containing cyclic compound as defined above,    4) obtainable by reacting (i) (A2) a divalent nickel compound, with (B) the nitrogen-containing cyclic compound as defined above, in the presence of a reducing agent, or    5) comprising (A) the nickel compound, and (B) the nitrogen-containing cyclic compound as defined above, with the proviso that said nitrogen-containing cyclic compound is not 1-methylimidazole nor 1,2-dimethylimidazole when said nickel compound is a hydrate of nickel chloride, bromide or iodide or nickel nitrate.    
   
   
       20 . A catalyst composition according to  claim 19 , which is the catalyst composition comprising (A) the nickel compound, (B) the nitrogen-containing cyclic compound, and a solvent, provided that said solvent is not a solvent consisting of ethanol and 2,2-dimethoxypropane.  
   
   
       21 . A catalyst composition according to  claim 20 , wherein the solvent is an organic solvent, provided that the organic solvent is not a solvent consisting of ethanol and 2,2-dimethoxypropane.  
   
   
       22 . A catalyst composition according to  claim 19 , which is the catalyst composition comprising (A) the nickel compound, (B) the nitrogen-containing cyclic compound, and a solvent consisting essentially of an aprotic organic solvent.  
   
   
       23 . A catalyst composition according to  claim 22 , wherein the aprotic organic solvent is ether or hydrocarbon.  
   
   
       24 . A catalyst composition according to  claim 19 , which is the catalyst composition comprising (A1) a zero valent nickel compound, and (B) the nitrogen-containing cyclic compound.  
   
   
       25 . A catalyst composition according to  claim 24 , wherein the zero valent nickel compound is bis(1,5-cyclooctadiene)nickel.  
   
   
       26 . A catalyst composition according to  claim 19 , which is the catalyst composition obtainable by reacting (i) (A2) a divalent nickel compound, with (B) the nitrogen-containing cyclic compound, in the presence of a reducing agent.  
   
   
       27 . A catalyst composition according to  claim 26 , wherein the divalent nickel compound is nickel(II) chloride, nickel(II) nickel bromide, nickel(II) iodide, nickel(II) nitrate, or nickel(II) acetate, and the reducing agent is an alkyl lithium or an alkyl Grignard reagent.  
   
   
       28 . A catalyst composition according to  claim 19 , which is the catalyst composition comprising (A) the nickel compound, and (B) the nitrogen-containing cyclic compound, with the proviso that said nitrogen-containing cyclic compound is not 1-methylimidazole nor 1,2-dimethylimidazole when said nickel compound is a hydrate of nickel chloride, bromide or iodide or nickel nitrate.  
   
   
       29 . A catalyst composition according to  claim 19 , wherein 
 The nitrogen-containing cyclic compound is the nitrogen-containing cyclic compound of formula (I).    
   
   
       30 . A catalyst composition according to  claim 29 , wherein Q is the unsubstituted alkylene group.  
   
   
       31 . A catalyst composition according to  claim 29 , wherein Q is the unsubstituted alkenylene group.  
   
   
       32 . A catalyst composition according to  claim 29 , wherein Q is the substituted or unsubstituted 1,2-phenylene group.  
   
   
       33 . A catalyst composition according to  claim 29 , wherein Q is —N═N.  
   
   
       34 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is the substituted or unsubstituted pyridine or fused ring compound thereof of which conjugated acid has pKa of 5 or more.  
   
   
       35 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is the substituted pyrimidine or substituted or unsubstituted fused pyrimidine compound of which conjugate acid has pKa of 3 or more.  
   
   
       36 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is the enamine compound obtainable from a cyclic ketone compound and a cyclic secondary amine compound.  
   
   
       37 . A catalyst composition according to  claim 36 , wherein the cyclic ketone compound is cyclopentanone or cyclohexanone, and the cyclic secondary amine compound is pyrrolidine or piperidine.  
   
   
       38 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is the substituted or unsubstituted 2H-pyrrole, 3,4-dihydro-2H-pyrrole or 3H-pyrrole or fused ring compound thereof.  
   
   
       39 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is the substituted or unsubstituted N-hydrocarbyl-1,2,3-triazole or fused ring compound thereof.  
   
   
       40 . A catalyst composition according to  claim 19 , wherein the nickel compound is nickel(II) chloride, nickel(II) nickel bromide, nickel(II) iodide, nickel(II) nitrate, nickel bis(1,5-cyclooctadiene)nickel, or nickel(II) acetate.  
   
   
       41 . A catalyst composition according to  claim 19 , wherein the nitrogen-containing cyclic compound is N,N-dimethylaminopyridine, or 1,8-diazabicyclo[5.4.0]-7-undecene.