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Chemoselectivity of cobalt-catalysed carbonylation—A reliable platform for the synthesis of fluorinated benzoic acids
Authors:Vadim P. Boyarskiy  Tatiana S. Khaybulova  Yurii A. Simonov
Affiliation:a Saint-Petersburg State University, Chemistry Department, Staryj Petergof, Universitetskii pr., 26, 198504 S.-Petersburg, Russian Federation
b Institute of Applied Physics, Academy of Sciences of Moldova, Academiei str., 5 MD-2028 Chisinau, Republic of Moldova
c Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland
Abstract:The cobalt-catalysed methoxycarbonylation of polysubstituted bromo,fluoro- and chloro,fluorobenzenes and 1,2,4-trichlorobenzene with emphasis on the chemo- and regio-selectivity of the reaction is described. The structures of isolated products of 1,4-dichloro-2-fluorobenzene carbonylation were determined by single-crystal X-ray diffraction. The fact that the fluorine substituents in the studied compounds remain intact indicates in favor of the anion-radical activation of aryl halides by a cobalt catalyst. For the first time, a universal method of preparation of the various fluorobenzoic acid derivatives from available raw materials with a good yield has been elaborated.
Keywords:Carbonylation   Aryl halides   Cobalt carbonyl   Fluorinated benzoic acids   Crystal structure
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