60040-82-6Relevant articles and documents
Electrochemical reduction of methyl 2-bromomethylbenzoate at carbon cathodes in dimethylformamide containingwater
Allen, Caroline R.,Brown, Drew K.,Potts, Jessica L.,Ji, Chang
, p. G3069-G3072 (2013/07/05)
Cyclic voltammetry and controlled-potential electrolysis have been employed to examine the electrochemical reduction of methyl 2-bromomethylbenzoate at carbon cathodes in dimethylformamide (DMF) containing tetramethylammonium tetrafluoroborate (TMABF4). A cyclic voltammogram for the reduction of the substrate exhibits one irreversible cathodic wave with a peak potential of -1.45 V vs. SCE, which is due to the two-electron cleavage of the benzylic carbon-bromine bond. The corresponding reductive peak current also increases incrementally with the amount of water in DMF. Bulk electrolyses of methyl 2-bromomethylbenzoate have been carried out at -1.85 V vs. SCE with different concentrations of water in the solvent. The reduction process involves carbanion intermediates to afford various products including phthalide, which is generated via intramolecular cyclization that is affected by the presence of water. Detailed mechanism for the electrochemical reaction is proposed and further studied by isotope incorporation experiment.
REDUCTIVE COUPLING OF BENZYL HALIDES USING NICKEL(0)-COMPLEX GENERATED IN SITU IN THE PRESENCE OF TETRAETHYLAMMONIUM IODIDE, A SIMPLE AND CONVENIENT SYNTHESIS OF BIBENZYLS
Iyoda, Masahiko,Sakaitani, Masahiro,Otsuka, Hiroki,Oda, Masaji
, p. 127 - 130 (2007/10/02)
Zerovalent nickel complex generated in situ by reduction of NiBr2(PPh3)2 with zinc powder in the presence of Et4NI was found to be an effective catalyst for homo-coupling of benzyl halides.The catalytic reactions proceeded smoothly in various solvents under mild conditions to afford dehalogenative-coupling products in good to high yields.