Z. Cao, Jianchao Liu, Y. Chu
2019
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Journal
Chinese Journal of Organic Chemistry
Abstract
The electro-oxidation cyanation of p- methoxybenzyl alcohol ( p- MeOC 6 H 4 CH 2 OH) to prepare aryl nitriles was studied by using cyclic voltammetry (CV) and constant current electrolysis (CCE). The effects of the volume ratio of H 2 O, concentration of H 2 SO 4 , temperature, electrode materials, current density and solvents on the electro-chemical reaction were studied. The results showed that the yield of p- methoxylbenzonitrile ( p- MeOBN) was 90% in 0.15 mol•L - 1 H 2 SO 4 and 30% H 2 O-DMSO solution at 60 ℃ and 10 mA/cm 2 of current density when tetrabutylammonium perchlorate (Bu 4 NClO 4 ) was used as electrolyte. The CCE of aromatic benzyl alcohols with different p- and o -substituted analogs was investigated under the optimized reaction conditions, and the yields toward formation of the corresponding aryl nitriles were 61% ~ 92%. A plausible mechanism for the electro-oxidation cyanation procedure was proposed. A novel paired electrochemical method for the synthesis of aryl nitriles from aromatic benzyl alcohols with hydroxylamine (HAM) as “N” source and aldehyde in situ in undivided electrochemical cell was successfully developed.