Synthesis of aromatic acids via catalysed methyl formate-chloroarene reactions
Authors:
G. Jenner and A. Ben Taleb
Affiliation:
Laboratoire de Piézochimie Organique, Synthèse et Stéréoréactivité (URA CNRS 466), European Higher Institute of Chemistry, 1, rue Blaise Pascal - B.P. 296, 67008 Strasbourg France
Abstract:
Chlorobenzene and more generally, chloroarenes, can be converted into aromatic acids via catalytic reaction with aqueous methyl formate under biphasic conditions. The only efficient catalyst is [PdCl2(PCy3)2] (Cy = cyclohexyl). [RU3(CO)12] and ammonium formate improve yield and selectivity. The mechanism should involve oxidative addition of the C---Cl bond to a zero-valent Pd species followed by CO insertion. The palladium catalyst may also directly activate methyl formate. The procedure is convenient (no solvent, no initial pressurization) and at least as efficient as previously described methods.