Process for preparing biphenylamines from anilides by ruthenium catalysis

A process for preparing one or more biphenylamides of formula (Ia)

• in which
• R1 is hydrogen, hydroxyl, fluorine, chlorine, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio or C1-C4-haloalkyl,
• R2 is C1-C4-alkyl, C6-C10-aryl or C6-C10-aryl-CH2—, and
• X1 is hydrogen, C1-C3-alkyl, C1-C4-alkoxy, fluorine or chlorine,
• X2 is hydrogen, C1-C3-alkyl, C1-C4-alkoxy, fluorine or chlorine,
• X3 is hydrogen, C1-C3-alkyl, C1-C4-alkoxy, fluorine or chlorine,
• comprising reacting one or more
• anilides of formula (II)
• in which
• R1 and R2 are each as defined above,
• with an organoboron compound of formula (III)
• in which
• X1, X2 and X3 are each as defined above,
• and which is selected from one of the following groups consisting of:
• (I) boronic acids of formula (III) in which
• Q is a hydroxyl group,
• m is 2,
• p is 1,
• or the anhydrides, dimers or trimers of these boronic acids;
• (II) boronic acid derivatives of formula (III) in which
• Q is F, Cl, Br, I, C1-C4-alkyl, C6-C10-aryl, C1-C4-alkoxy or C6-C10-aryloxy,
• m is 2,
• p is 1;
• (III) borinic acids of formula (III) in which
• Q is OH, F, Cl, Br, I, C1-C4-alkyl, C6-C10-aryl, C1-C4-alkoxy or C6-C10-aryloxy,
• m is 1,
• p is 2;
• (IV) cyclic boronic esters of formula (III) in which
• Q is a C2-C3-alkyldioxy radical which, together with the boron atom to which it is bonded, forms a 5- or 6-membered ring optionally substituted by one or more C1-C4-alkyl radicals,
• m is 1,
• p is 1;
• (V) boronates of formula (III) in which
• Q is OH, F, Cl, Br, I, C1-C4-alkyl, C6-C10-aryl, C1-C4-alkoxy or C6-C10-aryloxy,
• m is 3,
• p is 1
• and the negative charge of the boronate anion is compensated for by a cation,
• (VI) triarylboranes of formula (III) in which
• m is 0,
• p is 3;
• and
• (VII) tetraarylborates of formula (III) in which
• m is 0,
• p is 4
• and the negative charge of the tetraarylborate anion is compensated for by a cation,
• in the presence of a catalyst system consisting of a ruthenium catalyst, an activator, an oxidizing agent and a metal sulphate.