Process for cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates

US5686608A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Steffen Haber · Landau, DE
• Javier Manero · Frankfurt, DE

Key dates

• Filing date: Apr 24, 1995
• Grant date: Nov 11, 1997
• Expiry date: Apr 24, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D401/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reaction PA1 a) at least one water-soluble complexing ligand and PA1 b) sufficient water for the reaction mixture to form an aqueous phase. The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction. The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.