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Electrocarboxylation of Benzyl Halides through Redox Catalysis on the Preparative Scale
Author(s) -
Scialdone Onofrio,
Galia Alessandro,
Silvestri Giuseppe,
Amatore Christian,
Thouin Laurent,
Verpeaux JeanNoel
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501499
Subject(s) - catalysis , halide , redox , yield (engineering) , chemistry , homogeneous , carboxylic acid , carbon fibers , kinetics , inorganic chemistry , photochemistry , organic chemistry , materials science , thermodynamics , physics , quantum mechanics , composite number , metallurgy , composite material
The electrocarboxylation of benzyl halides to the corresponding carboxylic acids through homogeneous charge‐transfer catalysis was investigated both theoretically and experimentally to determine the influence of the operative parameters on the yield of the process and on the catalyst consumption. Theoretical considerations, based on fast kinetics of redox catalysis, were confirmed by the electrocarboxylation of 1‐phenyl‐1‐chloroethane catalyzed by 1,3‐benzenedicarboxylic acid dimethyl ester performed at a carbon cathode under different operative conditions. We obtained high yields of the target carboxylic acid and experienced a low catalyst consumption by operating with optimized [RX] bulk /[CO 2 ] bulk and [RX] bulk /[catalyst] ratios.