Catalyst complex with carbene ligand

Abstract

Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.

We claim: 
     
         1 . A method for performing an olefin metathesis reaction, comprising the step of contacting an olefin with a catalytic complex of the formula: 
       
         
           
           
               
               
           
         
       
       wherein M is ruthenium;
 R is hydrogen; 
 R 1  is phenyl; 
 X and X 1  are independently selected from the group consisting of anionic ligands; 
 L is selected from the group consisting of phosphines, phosphites, phosphinites, phosphonites, and pyridines; and 
 L 1  is of the formula: 
 
       
         
           
           
               
               
           
         
       
       wherein Y and Y 1  are each independently an aryl group substituted with halogen, C 1 -C 5  alkyl groups, or C 1 -C 5  alkoxy groups; and 
       Z and Z 1  are independently selected from the group consisting of hydrogen, C 1 -C 20  alkyl, C 2 -C 20  alkenyl, C 2 -C 20  alkynyl, C 2 -C 20  alkoxycarbonyl, aryl, C 1 -C 20  carboxylate, C 1 -C 20  alkoxy, C 2 -C 20  alkenyloxy, C 2 -C 20  alkynyloxy, and aryloxy, each Z and Z 1  optionally being substituted with halogen, C 1 -C 5  alkyl groups, or C 1 -C 5  alkoxy groups. 
     
     
         2 . The method of  claim 1 , wherein Y and Y 1  are each independently an aryl group substituted with C 1 -C 5  alkyl groups; and Z and Z 1  are independently selected from the group consisting of hydrogen and C 1 -C 20  alkyl. 
     
     
         3 . The method of  claim 1 , wherein X and X 1  are each halide, CF 3 CO 2 , CH 3 CO 2 , CFH 2 CO 2 , (CH 3 ) 3 CO, (CF 3 ) 2 (CH 3 )CO, (CF 3 )(CH 3 ) 2 CO, PhO, MeO, EtO, tosylate, mesylate, brosylate or trifluoromethanesulfonate; L is selected from the group consisting of phosphines, phosphites, phosphinites, and phosphonites; Y and Y 1  are each independently an aryl group substituted with C 1 -C 5  alkyl groups; and Z and Z 1  are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, and sec-butyl. 
     
     
         4 . The method of  claim 1 , wherein X and X 1  are chloride; Y and Y 1  are each 2,4,6-trimethylphenyl; L is selected from phosphines; and Z and Z 1  are independently selected from hydrogen and methyl. 
     
     
         5 . The method of  claim 4 , wherein L is selected from trimethylphosphine, triphenylphosphine, triisopropylphosphine, tricyclohexylphosphine, and tricyclopentylphosphine. 
     
     
         6 . The method of  claim 4 , wherein L is tricyclohexylphosphine. 
     
     
         7 . The method of  claim 4 , wherein L is triphenylphosphine. 
     
     
         8 . The method of  claim 4 , wherein Z and Z 1  are hydrogen. 
     
     
         9 . The method of  claim 8 , wherein L is selected from trimethylphosphine, triphenylphosphine, triisopropylphosphine, tricyclohexylphosphine, and tricyclopentylphosphine. 
     
     
         10 . The method of  claim 8 , wherein L is tricyclohexylphosphine. 
     
     
         11 . The method of  claim 8 , wherein L is triphenylphosphine. 
     
     
         12 . The method of  claim 1 , wherein X and X 1  are chloride; Y and Y 1  are each 2,6-diisopropylphenyl; L is selected from phosphines; and Z and Z 1  are independently selected from hydrogen and methyl. 
     
     
         13 . The method of  claim 12 , wherein L is selected from trimethylphosphine, triphenylphosphine, triisopropylphosphine, tricyclohexylphosphine, and tricyclopentylphosphine. 
     
     
         14 . The method of  claim 12 , wherein L is tricyclohexylphosphine. 
     
     
         15 . The method of  claim 12 , wherein L is triphenylphosphine. 
     
     
         16 . The method of  claim 12 , wherein Z and Z 1  are hydrogen. 
     
     
         17 . The method of  claim 16 , wherein L is selected from trimethylphosphine, triphenylphosphine, triisopropylphosphine, tricyclohexylphosphine, and tricyclopentylphosphine. 
     
     
         18 . The method of  claim 16 , wherein L is tricyclohexylphosphine. 
     
     
         19 . The method of  claim 16 , wherein L is triphenylphosphine.