# US 10,246,408 B2 · Process for preparing biphenylamines from anilides by ruthenium catalysis

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- Number: US 10,246,408 B2
- Document ID: US10246408B2
- Status: Granted
- Kind: B2
- Application number: 16/113,624
- Filed: 2018-08-27
- Published: 2018-12-20
- Granted: 2019-04-02
- Earliest claimed: 2014-04-25
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience Aktiengesellschaft
- Inventors: Thomas Himmler; Lars Rodefeld; Jonathan Hubrich; Lutz Ackermann
- Web page: https://patentgrep.com/patent/US10246408B2

## CPC

- C07C 231/12: by reactions not involving the formation of carboxamide groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a novel process for preparing substituted biphenylamides of the general formula (V) characterized in that anilides of the formula (II) in a solvent other than tetrahydrofuran, are reacted with an organoboron compound of the formula (III) in the presence of a catalyst system consisting of a ruthenium catalyst, an activator, an oxidizing agent and a metal triflate.

## Claims

### Claim 1

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.