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US 2026/0200963 A1Published application
Novel iron-based compounds, processes for the preparation thereof, and use thereof as catalysts
AssigneesUniversite Paris-Saclay, Centre National De La Recherche Scientifique
InventorsJérôme HANNEDOUCHE, Sophie BEZZENINE, Richard GIL, Donghuang CHEN
Life of this patent
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Abstract
Iron anilido-imine complexes, methods for their preparation, their use as catalysts to catalyze the formation of carbon-carbon bonds, in particular, in the Suzuki-Miyaura reaction, and compounds prepared by with the iron anilido-imine complexes. The iron anilido-imine complexes provide stable catalysts with respect to the ambient air, thereby allowing the creation of the carbon-carbon bonds.
Claims21
-22. (canceled)
A method for the implementation of a coupling reaction with the use as catalyst of at least one compound of the following general formula (I):
- in which:
- A is chosen from:
- a —X group in which X is chosen from
- a chlorine atom,
- a bromine atom, and
- a group
- in which:
- M is a coordinating solvent, and
- p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4,
- a group
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and
- G is chosen from
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atom(s).
14 more elements
A compound, of the following general formula (I):
- A is chosen from:
- a —X group in which X is chosen from
- a chlorine atom,
- a bromine atom, and
- a group
- in which:
- M is a coordinating solvent, and
- p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4,
- a group
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- when A corresponds to the group
- then R1, R5, R6, and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 or 2 or 4 to 10 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and R2, R3, R4, R7, R8 and R9, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- when A corresponds to the —X group or the group
- then R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and
- G is chosen from:
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atoms
- excluding the compound of the following formula:
19 more elements
A process for preparing a compound of formula (I):
- in which:
- A is chosen from:
- a —X group in which X is chosen from
- a chlorine atom,
- a bromine atom, and
- a group
- in which:
- M is a coordinating solvent, and
- p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4,
- a group
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atom(s), in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and
- G is chosen from:
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atom(s),
- and
- in the case the compound of formula (I) is a compound of formula (Ia):
- in which:
- X is chosen from:
- a chlorine atom, and
- a bromine atom,
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and
- G is chosen from:
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atom(s),
- then the method comprises:
- (a) a condensation step of a compound of formula (V)
- in which in which B, C, D, and E have the meanings defined above, and F is a fluorine atom,
- on a compound of formula (VI):
- in which R1, R2, R3, R4, and R5 have the meanings defined above,
- to obtain the compound of formula (III)
- in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings defined above, and F is a fluorine atom,
- (b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):
- in which R6, R7, R8, R9, and R10 have the meanings defined above
- to obtain the compound of formula (II)
- in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings defined above,
- c) a sequential addition step of n-butyl lithium and then iron (II) halide FeX2 on said compound of formula (II) to obtain the compound of formula (Ia),
- or
- in the case the compound of formula (I) isa compound of formula (Ib):
- in which:
- X is chosen from:
- a chlorine atom, and
- a bromine atom
- M is a coordinating solvent,
- p is chosen from 1, 2, 3, 4 or a decimal number that can vary from a value greater than 0 but less than 4,
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 10 carbon atoms,
- R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched Alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atoms, and
- G is chosen from:
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atom(s),
- then the method comprises:
- a) a condensation step of a compound of formula (V)
- in which in which B, C, D, and E have the meanings defined above and F is a fluorine atom,
- on a compound of formula (VI):
- in which R1, R2, R3, R4, and R5 have the meanings defined above,
- to obtain the compound of formula (III)
- in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings defined above, and F is a fluorine atom,
- (b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):
- in which R6, R7, R8, R9 and R10 have the meanings defined above,
- to obtain the compound of formula (II)
- in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings defined above,
- (c) a sequential addition step of n-butyl lithium and then iron (II) halide FeX2 on said compound of formula (II) to obtain the compound of formula (Ib), or in the case the compound of formula (I) isa compound of formula (Ic):
- in which:
- B, C, D, and E, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 2 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atoms, or a linear or branched dialkylamino group of 2 to 20 carbon atoms,
- R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, identical or different, are chosen from:
- a hydrogen atom, a halogen, in particular F or Cl, a trifluoromethyl group CF3, a linear or branched alkyl group of 1 to 10 carbon atoms, in particular a linear or branched alkyl group of 1 to 4 carbon atoms, a linear or branched alkoxy group of 1 to 10 carbon atom(s) or a linear or branched dialkylamino group of 2 to 20 carbon atom(s), and
- G is chosen from:
- a hydrogen atom, and
- a linear or branched alkyl group of 1 to 5 carbon atom(s),
- then the method comprises:
- a) a condensation step of a compound of formula (V)
- in which B, C, D, and E have the meanings defined above, and F is a fluorine atom on a compound of formula (VI):
- in which R1, R2, R3, R4, and R5 have the meanings defined above to obtain the compound of formula (III)
- in which B, C, D, E, G, R1, R2, R3, R4, and R5 have the meanings defined above, and F is a fluorine atom
- (b) an aromatic nucleophilic substitution step of said compound of formula (III) on a compound of formula (IV):
- in which R6, R7, R8, R9 and R10 have the meanings defined above,
- to obtain the compound of formula (II)
- in which B, C, D, E, G, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 have the meanings defined above, and
- (c) a step of sequential addition of n-butyl lithium and then iron (III) tris-acetylacetone on said compound of formula (II) to obtain said compound of formula (Ic).
84 more elements
Dependencies are inferred from the claim text.