Catalysts for the alkyne metathesis

Alkylidyne complexes of the general Formula 25

• wherein
• M is selected from Mo or W,
• the substituents R9, R10, R11 may be equal or may be different from one another and are independently selected from one another from the following groups:
• C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, with the proviso that at least one of said substituents is a 6-18 membered aryl or 5-10 membered heteroaryl residue, wherein said aryl or heteroaryl residue at the silicon in turn has up to five identical or different substituents, from the list:
• H, C1-C12-alkyl, C1-C12-alkvloxy, di-C1-C4-alkylamino, C3-C12-cycloalkyl, C3-C12-cycloalkyloxy, 6-18 membered aryl, 5-10 membered heteroaryl, or halogen, and,
• R15 is selected from C1-C12 alkyl, C3-C12 cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl.

Use of the compounds of Formula 25 and the adducts with solvents thereof

• wherein
• M is selected from Mo or W,
• the substituents R9, R10, R11 may be equal or may be different from one another and are independently selected from one another from the following groups:
• C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, with the proviso that at least one of said substituents is a 6-18 membered aryl or 5-10 membered heteroaryl residue, wherein said aryl or heteroaryl residue at the silicon in turn has up to five identical or different substituents, from the list:
• H, C1-C12-alkyl, C1-C12-alkvloxy, di-C1-C4-alkylamino, C3-C12-cycloalkyl, C3-C12-cycloalkyloxy, 6-18 membered aryl, 5-10 membered heteroaryl, or halogen, and
• R15 is selected from C1-C12 alkyl, C3-C12 cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl,
• as catalysts for the alkyne metathesis.

Method of preparing the compounds of Formula I

• wherein
• M is selected from Mo or W,
• the substituents Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh may be equal or may be different from one another and are selected independently from one another from:
• H, C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, 5-10 membered heteroaryl, C1-C12-alkyloxy, C3-C12-cycloalkyloxy, C6-C20-aryloxy, di-C1-C4-alkylamino, halogen, nitro, cyano, trifluoromethyl, or —COOR12, wherein R12 is selected from C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl,
• and the substituents Ra and Rb or Rb and Rc or Rc and Rd and Rh and Rg or Rg and Rf or Rf and Re may optionally also be linked together while forming a saturated, unsaturated or aromatic ring, and/or the residues Rd and Re may optionally be linked together while forming a 5-8 membered saturated, unsaturated or aromatic ring,
• the substituents R9, R10, R11 may be equal or may be different from one another and are independently selected from one another from the following groups:
• C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, with the proviso that at least one of said substituents is a 6-18 membered aryl or 5-10 membered heteroaryl residue, wherein said aryl or heteroaryl residue at the silicon in turn has up to five identical or different substituents, from the list:
• H, C1-C12-alkyl, C1-C12-alkyloxy, di-C1-C4-alkylamino, C3-C12-cycloalkyl, C3-C12-cycloalkyloxy, 6-18 membered aryl, 5-10 membered heteroaryl, or halogen, and X is selected from N or CR13, wherein R13 is selected from C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl
• in which a compound of the general Formula 18
• is reacted with a compound of the general Formula 19

Method for carrying out alkyne metathesis reactions, in which a compound of the general Formula I

• wherein
• M is selected from Mo or W,
• the substituents Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh may be equal or may be different from one another and are selected independently from one another from:
• H, C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, 5-10 membered heteroaryl, C1-C12-alkyloxy, C3-C12-cycloalkyloxy, C6-C20-aryloxy, di-C1-C4-alkylamino, halogen, nitro, cyano, trifluoromethyl, or —COOR12, wherein R12 is selected from C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, and the substituents Ra and Rb or Rb and Rc or Rc and Rd and Rh and Rg or Rg and Rf or Rf and Re may optionally also be linked together while forming a saturated, unsaturated or aromatic ring, and/or the residues Rd and Re may optionally be linked together while forming a 5-8 membered saturated, unsaturated or aromatic ring,
• the substituents R9, R10, R11 may be equal or may be different from one another and are independently selected from one another from the following groups:
• C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, with the proviso that at least one of said substituents is a 6-18 membered aryl or 5-10 membered heteroaryl residue, wherein said aryl or heteroaryl residue at the silicon in turn has up to five identical or different substituents, from the list:
• H, C1-C12-alkyl, C1-C12-alkyloxy, di-C1-C4-alkylamino, C3-C12-cycloalkyl, C3-C12-cycloalkyloxy, 6-18 membered aryl, 5-10 membered heteroaryl, or halogen, and X is selected from N or CR13, wherein R13 is selected from C1-C12-alkyl, C3-C12-cycloalkyl, 6-18 membered aryl, or 5-10 membered heteroaryl, is reacted in presence of a metal salt.