Biaryl Synthesis via Pd-Catalyzed Decarboxylative Coupling of Aromatic Carboxylates with Aryl Halides

• DOI: 10.1021/ja068993+
• Publication Date: 2007-03-22T10:45:54Z
• Authors: Lukas J. Goossen; Nuria Rodríguez; Bettina Melzer; Christophe Linder; Guojun Deng; Laura M. Levy
• Keywords: Decarboxylation; Bimetallic strip; Potassium carbonate

A new strategy for the regiospecific construction of unsymmetrical biaryls is presented, in which easily available salts carboxylic acids are decarboxylated situ to give arylmetal species that serve as nucleophilic component a catalytic cross-coupling reaction with aryl halides. The catalyst system consists copper phenanthroline complex mediates extrusion CO2 from aromatic carboxylates generate arylcopper species, and palladium catalyzes these intermediates This bimetallic allows direct coupling various aryl, heteroaryl, or vinyl heteroaryl iodides, bromides, chlorides at 160 degrees C presence mild base such potassium carbonate. present scope potential economic impact demonstrated by synthesis 42 biaryls, some substantial industrial relevance. Remaining challenges future perspectives transformation discussed.