Process for homogeneously catalyzed c-c coupling reaction

摘要

The invention relates to a process for carrying out a homogeneously catalyzed C—C coupling reaction between an optionally substituted (hetero)aromatic bromide compound and a second reactant, which is chosen from the group of olefins in which at least one of the substituents on the olefinic sp² carbon atoms is a hydrogen atom, and the group of organoboron compounds with the formula Ar—B(OR¹)—OR², where Ar stands for an optionally substituted (hetero)aryl group and R¹ and R² each independently represent H or an alkyl group or, together with the O-atoms to which they are bound and the B-atom, form a ring with 2-5 C-atoms, in the presence of an aprotic dipolar solvent and a base, a palladium salt without a ligand being used as palladium catalyst and the reaction being carried out at a ratio between the quantity of palladium present in the palladium salt and the optionally substituted (hetero)aromatic bromine compound of between 0.00001 and 0.1 mol %, preferably between 0.01 and 0.1 mol %. Preferably the optionally substituted (hetero)aromatic bromide compound contains at least one hetero atom chosen from N, O and S. The second reactant is preferably an optionally substituted, aliphatic olefin with 2-5 carbon atoms, an olefin substituted with a carboxyl group, a carboxyester, a nitrile, an optionally substituted amido group, a nitro group or a halogenated hydrocarbon. In another embodiment the second reactant is preferably an aryl boric acid. As aprotic dipolar solvent dimethylformamide or N-methylpyrrolidinone is preferably chosen.