Catalysts with a silylene ligand
A metal complex including at least one metal atom chosen from the metals of Groups 8, 9 and 10 of the Periodic Table of the Elements and one or more ligands, wherein at least one ligand includes a cyclic silylene structure and a Lewis base which donates an electron pair to the silicon atom of the cyclic silylene structure.
1. A metal complex comprising at least one Pt atom wherein at least one ligand comprises a cyclic silylene structure which is a silacyclopropylidene and a Lewis base which donates an electron pair to the silicon atom of said cyclic silylene structure, said cyclic silyene structure being a compound of formula (III):
where
B represents the Lewis base, which is selected from the group consisting of
where
each R c independently represents
a hydrogen atom,
a halogen atom, or
a group chosen from:
an alkyl group,
a haloalkyl group,
a cycloalkyl group, optionally substituted one or more times by a halogen atom and/or by an alkyl group,
a cycloalkylalkyl group, optionally substituted one or more times on the cycloalkyl part and/or on the alkyl part by a halogen atom and/or by an alkyl group,
an aryl group, optionally substituted one or more times by a halogen atom and/or by an alkyl group,
an arylalkyl group, optionally substituted one or more times on the aryl part and/or on the alkyl part by a halogen atom and/or by an alkyl group,
an acyl group,
an amine group, and
a hydroxyl group;
and each R b is independently chosen from:
a hydrogen atom,
a halogen atom,
an alkyl group, optionally substituted one or more times
by a halogen atom,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
a cycloalkyl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
a cycloalkylalkyl group, optionally substituted one or more times on the cycloalkyl part and/or on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an aryl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an arylalkyl group, optionally substituted one or more times on the aryl part and/or on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an acyl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an hydroxyl group,
an alkoxy group, optionally substituted one or more times on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an amine, imine or amide group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group, and
a phosphine, phosphite, phosphorane or phosphorus ylide group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group; wherein
in each R b group comprising carbon atoms, one or more of the carbon atoms is optionally replaced by a silicon atom,
each R b group optionally comprises one or more unsaturations, and
optionally, two groups or more chosen from the R b groups, with the atoms to which they are bonded, bond to form a monocyclic or polycyclic ring group, where the monocyclic ring group or the polycyclic ring group
consists of 3 to 20 ring members,
optionally comprises one or more unsaturations,
optionally comprises one or more heteroatoms chosen from O, N, Si and P, and
is optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group.
2. The metal complex as claimed in claim 1 , wherein the Lewis based included in said ligand is bonded to at least one atom of the cyclic silylene structure other than the silicon atom in the silylene form.
3. The metal complex as claimed in claim 1 , wherein said ligand comprising a cyclic silylene structure and a Lewis base which donates an electron pair to the silicon atom of said cyclic silylene structure is the compound of formula (VI):
in which the symbol “Q” represents
and
the symbol “Ary” represents
4. The metal complex as claimed in claim 1 , wherein the metal complex is the compound of formula (VII):
in which the symbol “Q” represents
and
the symbol “Ary” represents
5. The metal complex as defined in claim 1 is used as catalyst.
6. The metal complex claimed in claim 5 , is used as catalyst for hydrosilylation reaction.
7. A process for the hydrosilylation of an unsaturated compound comprising at least one alkene functional group and/or at least one alkyne functional group with a compound comprising at least one hydrosilyl functional group, said process is catalyzed by a metal complex as defined in claim 1 .
8. The process as claimed in claim 7 , in which the compound comprising at least one hydrosilyl functional group is chosen from the group consisting of:
a silane or polysilane compound comprising at least one hydrogen atom bonded to a silicon atom;
a siloxane compound comprising at least one hydrogen atom bonded to a silicon atom per molecule, at least two hydrosilyl functional groups;
an organic polymer comprising hydrosilyl functional groups at the terminal positions.
9. A composition comprising:
at least one unsaturated compound comprising at least one alkene functional group and/or at least one alkyne functional group,
at least one compound comprising at least one hydrosilyl functional group, and
a catalyst chosen from the metal complexes as defined in claim 1 .
10. The composition as claimed in claim 9 , wherein the concentration of catalyst in the composition is less than 10 ppm by weight.
11. The metal complex as claimed in claim 1 , wherein the cyclic silylene structure is a compound of formula (IV):
where
each R b is as defined above;
R d —B is a radical obtained by substituting, by B, a group chosen from:
an alkyl group, optionally substituted one or more times
by a halogen atom,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
a cycloalkyl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
a cycloalkylalkyl group, optionally substituted one or more times on the cycloalkyl part and/or on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an aryl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an arylalkyl group, optionally substituted one or more times on the aryl part and/or on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an acyl group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an alkoxy group, optionally substituted one or more times on the alkyl part
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group,
an amine, imine or amide group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a haloalkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group, and
a phosphine, phosphite, phosphorane or phosphorus ylide group, optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group; and
B is defined in claim 1 .
12. The metal complex as claimed in claim 1 , wherein the cyclic silylene structure is a compound of formula (V):
where
each R b is as defined above; and
each R e independently represents a group chosen from
a hydrogen atom,
a halogen atom, or
a group chosen from:
an alkyl group,
a haloalkyl group,
a cycloalkyl group, optionally substituted one or more times by a halogen atom and/or by an alkyl group,
a cycloalkylalkyl group, optionally substituted one or more times on the cycloalkyl part and/or on the alkyl part by a halogen atom and/or by an alkyl group,
an aryl group, optionally substituted one or more times by a halogen atom and/or by an alkyl group,
an arylalkyl group, optionally substituted one or more times on the aryl part and/or on the alkyl part by a halogen atom and/or by an alkyl group,
an acyl group, and
an hydroxyl group; wherein
optionally, two groups or more chosen from the R e and R b groups, with the atoms to which they are bonded, bond to form a monocyclic or polycyclic ring group, where the monocyclic ring group or the polycyclic ring group
consists of 3 to 20 ring members,
optionally comprises one or more unsaturations,
optionally comprises one or more heteroatoms chosen from O, N, Si and P, and
is optionally substituted one or more times
by a halogen atom,
by an alkyl group,
by a cycloalkyl group,
by a cycloalkylalkyl group,
by an aryl group,
by an arylalkyl group,
by an acyl group,
by an amine group,
by an hydroxyl group, or
by an alkoxy group.