Olefin Metathesis
AssigneeTechnische Universitat Graz
InventorsChristian Slugovc, Julia Wappel
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Abstract
The present invention relates to pre-catalysts for olefin metathesis and composition involving these pre-catalysts.
Claims19
A compound having general formula (I)
- wherein X1 is selected from the group consisting of halogens, preferably Cl, Br or I, pseudohalogens, trifluoroacetic acid, carboxylates and a κ2 (N5O) bound 8-quinolinlate of the general formula (II)
- Q1, Q2, Q3, Q4, Q5 and Q6 are independently selected from the group consisting of hydrogen, halogens, cyano, C1 to C6-alkyl,aryl, benzyl, nitro,hydroxyl, sulfonic acid, arylsulfonyl, —ORa, —NRa2, —CXb3, and —CORa, whereas Ra H or C1 to C6-alkyl (preferably C1 to C3-alkyl) and Xb is F, Cl or Br,
- Y1 and Y2 are independently selected from the group consisting of hydrogen C1 to C6-alkyl, aryl,
- wherein
- X3 is selected from the group consisting of hydrogen, —OR6, —COH, —COR6, —COOR6—SR6, SOR6, SO2R6, wherein R6 is optionally a functionalized, branched or unbranched C1 to C6-alkyl group
- R7, R8, R9 and R10 is independently selected from the group consisting of hydrogen, C1 to C6 alkyl (preferably C1 to C3-alkyl), halogens, nitro and C1 to C6-alkoxy, particularly —OCH3, whereas two adjacent substituents can form an additional aromatic ring with each other (e.g. substituted or unsubstituted indenylidene rings),
- R11 is a substituted or unsubstituted aryl group, NHC is a N-heterocyclic carbene and
- Me is a metal selected out of the group of ruthenium, molybdenum and tungsten.
A compound having general formula (I)
- wherein
- X1 κ2 (N,O) is a κ2 (N,O) bound 8-quinlionlate of the general formula (II)
- Q1, Q2, Q3, Q4, Q5 and Q6 are independently selected from the group consisting of hydrogen, halogens, cyano, C1 to C6-alkyl aryl, benzyl, nitro, hydroxyl, sulfonic acid, arylsulfonyl, —ORa, —NRa2, —CXb3, and —CORa, whereas Ra H or C1 to C6-alkyl (preferably C1 to C3-alkyl) and Xb is F, Cl or Br,
- Y1 and Y2 are independently selected from the group consisting of hydrogen C1 to C6-alkyl, aryl,
- wherein
- X3 is selected from the group consisting of hydrogen, —OR6, —COH, —COR6, —COOR6—SR6, SOR6, SO2R6, wherein R6 is optionally a functionalized, branched or unbranched C1 to C6-alkyl group
- R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, C1 to C6 alkyl, halogen, nitro and C1 to C6-alkoxy, particularly —OCH3, wherein two adjacent substituents can form an additional aromatic ring with each other
- R11 is a substituted or unsubstituted aryl group,
- NHC is a N-heterocyclic carbene and
- Me is a metal selected out of the group of ruthenium, molybdenum and tungsten.
A method for olefin metathesis, particularly for ring opening metathesis polymerization of cyclic olefins in the presence of a compound comprising a step of bringing into contact at least one olefin with a compound, wherein the olefin metathesis is initiated via the addition of acid, whereas the olefin metathesis is most preferable the ring opening metathesis polymerization of dicyclopentadiene, wherein the compound has the general formula (I)
- wherein X1 is selected from the group consisting of halogens, preferably Cl, Br or I, pseudohalogens, trifluoroacetic acid, carboxylates and a κ2 (N,O) bound 8-quinolinlate of the general formula (II)
- Q1, Q2, Q3, Q4, Q5 and Q6 are independently selected from the group consisting of hydrogen, halogens, cyano, C1 to C6-alkyl,aryl, benzyl, nitro,hydroxyl, sulfonic acid, arylsulfonyl, —ORa, —NRa2, —CXb3, and —CORa, whereas Ra H or C1 to C6-alkyl (preferably C1 to C3-alkyl) and Xb is F, Cl or Br,
- Y1 and Y2 are independently selected from the group consisting of hydrogen C1 to C6-alkyl, aryl,
- wherein
- X3 is selected from the group consisting of hydrogen, —OR6, —COH, —COR6, —COOR6—SR6, SOR6, SO2R6, wherein R6 is optionally a functionalized, branched or unbranched C1 to C6-alkyl group
- R7, R8, R9 and R10 is independently selected from the group consisting of hydrogen, C1 to C6 alkyl (preferably C1 to C3-alkyl), halogens, nitro and C1 to C6-alkoxy, particularly —OCH3, whereas two adjacent substituents can form an additional aromatic ring with each other (e.g. substituted or unsubstituted indenylidene rings),
- R11 is a substituted or unsubstituted aryl group, NHC is a N-heterocyclic carbene and
- Me is a metal selected out of the group of ruthenium, molybdenum and tungsten.
A method for olefin metathesis, particularly for ring opening metathesis polymerization of cyclic olefins in the presence of a compound comprising a step of bringing into contact at least one olefin with a compound, wherein the olefin metathesis is initiated via the addition of acid, whereas the olefin metathesis is most preferable the ring opening metathesis polymerization of dicyclopentadiene, wherein the compound has the general formula (I)
- wherein X1 κ2 (N,O) is a κ2 (N,O) bound 8-quinlionlate of the general formula (II)
- Q1, Q2, Q3, Q4, Q5 and Q6 are independently selected from the group consisting of hydrogen, halogens, cyano, C1 to C6-alkyl aryl, benzyl, nitro, hydroxyl, sulfonic acid, arylsulfonyl, —ORa, —NRa2, —CXb3, and —CORa, whereas Ra H or C1 to C6-alkyl (preferably C1 to C3-alkyl) and Xb is F, Cl or Br,
- Y1 and Y2 are independently selected from the group consisting of hydrogen C1 to C6-alkyl, aryl,
- wherein X3 is selected from the group consisting of hydrogen, —OR6, —COH, —COR6, —COOR6—SR6, SOR6, SO2R6, wherein R6 is optionally a functionalized, branched or unbranched C1 to C6-alkyl group
- R7, R8, R9 and R10 are independently selected from the group consisting of hydrogen, C1 to C6 alkyl, halogen, nitro and C1 to C6-alkoxy, particularly —OCH3, wherein two adjacent substituents can form an additional aromatic ring with each other
- R11 is a substituted or unsubstituted aryl group,
- NHC is a N-heterocyclic carbene and
- Me is a metal selected out of the group of ruthenium, molybdenum and tungsten.
Dependencies are inferred from the claim text.