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Paired Electro‐Synthesis of Remote Amino Alcohols with/in H<sub>2</sub>O

Xinyue Fang, Xinwei Hu, Quan‐Xin Li, Shao‐Fei Ni, Zhixiong Ruan

2024Angewandte Chemie International Edition25 citationsDOIOpen Access PDF

Abstract

Amino alcohols, particularly remote amino alcohols and peptide alcohols, are valuable due to their functional diversity in biologically active compounds. However, traditional synthesis methods face significant challenges, making electrochemistry an attractive alternative. We have developed a mild and biocompatible sequential paired electrolysis strategy, leveraging copper-electrocatalysis to synthesize diverse remote amino alcohols, including unnatural peptide alcohols. Both experimental results and density functional theory (DFT) calculations demonstrated that water serves as both the hydroxyl source and the solvent, facilitating the generation of CuH with Cu(I) at the cathode, which in turn reduces the aldehyde intermediates formed during the reaction.

Topics & Concepts

ElectrolysisAmino acidAldehydeElectrocatalystCombinatorial chemistryElectrochemistryChemistryAlcohol oxidationCathodeDensity functional theorySolventPeptideAlcoholCatalysisOrganic chemistryComputational chemistryBiochemistryElectrodeElectrolytePhysical chemistryElectrocatalysts for Energy ConversionCO2 Reduction Techniques and CatalystsElectrochemical Analysis and Applications