Compounds and the use thereof in metathesis reactions

Abstract

The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula: wherein: M is a Group 6 metal atom; X is an oxygen atom, ═N—R 5 , ═N—N(R 5 )(R 5′ ) or ═N—O—R 5 , R 5 and R 5′ independently being various substituents, such as aryl or heteroaryl, each optionally substituted; n is 0 or 1; R z is a neutral ligand; R 1 is hydrogen or an organic substituent; R 2 is an aryl or heteroaryl group, each optionally substituted; R 3 is an anionic ligand; and R 4 is an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted.

1 . A compound of Formula (II) 
       
         
           
           
               
               
           
         
       
       wherein:
 M is a molybdenum atom or a tungsten atom; 
 R 101  is phenyl, alkyl, or cycloalkyl, each of which is optionally substituted; 
 R 102  pyrrolyl or indolyl, each of which is optionally substituted; 
 R 103  is phenyl, optionally substituted; 
 R 104  is a hydrogen atom; 
 R105 is —O—(C 1-6  alkyl) or —CH 2 —O—(C 1-6  alkyl); and 
 R 106  and R 107  are independently a hydrogen atom, C 1-6  alkyl, C 1-6  alkoxy, or a halogen atom. 
 
     
     
         2 . The compound of  claim 1 , wherein R 101  is phenyl, 2,6-dichlorophenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, 2-trifluoromethylphenyl, pentafluorophenyl, tert-butyl, or 1-adamantyl. 
     
     
         3 . The compound of  claim 1 , wherein R 102  is pyrrol-1-yl, 2,5-dimethylpyrrol-1-yl, 2,5-diphenylpyrrol-1-yl, or indol-1-yl. 
     
     
         4 . The compound of  claim 1 , wherein R 103  is 2,6-diphenylphenyl or 4-bromo-2,3,5,6-tetraphenylphenyl, or
 wherein R 103  is:   
       
         
           
           
               
               
           
         
       
       wherein “iPr” refers to isopropyl, and “OTBDMS” refers to tert-butyldimethylsilyloxy. 
     
     
         5 . The compound of  claim 1 , wherein R 105  is methyloxy, ethyloxy, or isopropyloxy. 
     
     
         6 . The compound of  claim 1 , wherein R 106  and R 107  are independently a hydrogen atom, methyl, a halogen atom, or methyloxy. 
     
     
         7 . A method for carrying out a metathesis reaction, the method comprising:
 providing a first compound having one or more carbon-carbon double bonds; and   reacting the first compound via a metathesis reaction in the presence of a compound of  claim 1 .   
     
     
         8 . The method of  claim 7 , wherein the first compound has two or more carbon-carbon double bonds. 
     
     
         9 . The method of  claim 8 , wherein the metathesis reaction is a ring-closing metathesis reaction between two of the two or more carbon-carbon double bonds of the first compound. 
     
     
         10 . A method of carrying out a metathesis reaction, the method comprising:
 providing a first compound having one or more carbon-carbon double bond and a second compound having one or more carbon-carbon double bonds; and   reacting the first compound and the second compound via a metathesis reaction in the presence of a compound of  claim 1 .   
     
     
         11 . The method of  claim 10 , wherein the first compound and the second compound are the same compound. 
     
     
         12 . The method of  claim 10 , wherein the first compound and the second compound are not the same. 
     
     
         13 . The method of  claim 12 , wherein the first compound is an internal olefin. 
     
     
         14 . The method of  claim 13 , wherein the second compound is a short-chain alkene. 
     
     
         15 . The method of  claim 14 , wherein the short-chain alkene is ethylene. 
     
     
         16 . The method of  claim 11  wherein the first compound is an unsaturated ester. 
     
     
         17 . The method of  claim 15 , wherein the first compound is an unsaturated ester. 
     
     
         18 . The compound of  claim 1 , wherein M is a tungsten atom. 
     
     
         19 . The compound of  claim 1 , wherein:
 M is a tungsten atom;   R 101  is 2,6-dichlorophenyl;   R 102  is 2,5-dimethylpyrrol-1-yl;   R 103  is:   
       
         
           
           
               
               
           
         
         R 104  is hydrogen; 
         R 105  is methyloxy; 
         R 106  is hydrogen; and 
         R 107  is hydrogen. 
       
     
     
         20 . The compound of  claim 1 , comprising a neutral ligand.