Iron catalyzed cross coupling reactions of aromatic compounds

US7026478B2 · kind B2 · utility

Assignee

• Studiengesellschaft Kohle gGmbH · DE

Inventors

• Alois Fürstner · Neheim, DE
• Andreas Leitner · New Castle, US
• Maria Magdalena Mendez · Wetter (Ruhr), DE

Key dates

• Filing date: May 10, 2002
• Grant date: Apr 11, 2006
• Expiry date: Jul 11, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D487/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the production of compounds Ar—R1 by means of a cross-coupling reaction of an organometallic reagent R1-M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.