Iron-copper co-catalyzed process for carbon-carbon or carbon-heteroatom bonding

摘要

The present invention relates to a process for creating a Carbon-Carbon bond (C—C) or a Carbon-Heteroatom bond (C-HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C—C or C-HE bond, wherein the reaction takes place in the presence of an effective quantity of a catalytic system comprising iron and copper.

主权项

1. A process for creating a compound of formula (III):the process comprising:
reacting, in the presence of an effective quantity of a catalytic system comprising iron and copper, a compound of formula (IIc): wherein in formula (IIc):
E represents a residue of a cycle compound, containing 4, 5 or 6 carbon atoms in its cycle, optionally substituted, and representing at least one of the following cycles: a monocyclic or polycyclic aromatic carbocycle, the polycyclic aromatic carbocycle selected from the group consisting of a compound constituted by at least 2 aromatic carbocycles and between them forming ortho- or ortho- and peri-condensed systems, and a compound constituted by at least 2 carbocycles only one of which is aromatic and between them forming ortho- or ortho- and peri-condensed systems; or a monocyclic aromatic heterocycle having at least one of heteroatoms P, O, N or S, or a polycyclic aromatic heterocycle, selected from the group consisting of a compound constituted by at least 2 heterocycles having at least one heteroatom in each cycle wherein at least one of the two cycles is aromatic and bet ween them forming ortho- or ortho- and peri-condensed systems, and a compound constituted by at least one carbocycle and at lead one heterocycle at least one of the cycles being aromatic and for between them ortho- or ortho- and peri-condensed systems;
R37, which may be identical or different, represents substituents on the cycle;Y represents a halogen atom or a group of formula —OSO2—Re, in which Re is a hydrocarbon group; andn″ represents the number of substituents on the cycle and is 0, 1, 2, 3, 4 or 5, with a nucleophilic compound of formula (Ik): wherein in formula (Ik):
A represents the residue of a cycle forming all or a portion of a monocyclic or polycyclic, aromatic or non aromatic heterocyclic system, wherein one of the carbon atoms is replaced by at least one nucleophilic atom selected from the group consisting of a nitrogen, sulfur and phosphorus atom;R22 represents C1-C6 alkyl, C2-C6 alkenyl or alkynyl, C1-C6 alkoxy or thioether, cyclohexyl, phenyl, benzyl, a group or function such as hydroxyl, thiol, carboxyl, ester, amide, formyl, acyl, aroyl, amide, urea, isocyanate, thioisocyanate, nitrile, azide, nitro, sulfone, sulfonic, halogen, pseudo-halogen or trifluoromethyl; andn represents the number of substituents on the cycle and is 0, 1, 2, 3 or 4.