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Updated: Jul 24, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Electroreductive Access to 1,2-Aminoalcohols via Cross Aza-Pinacol Coupling of N-Acyl Diarylketimines and Aldehydes
Dongmin Kwak1,2, Sehwa Jung3, Hyeonbin Ha1
1Infectious Diseases Therapeutic Research Center, Korea Research Institute of Chemical Technology (KRICT), Daejeon 34114, Republic of Korea.
Abstract:
We present highly efficient and operationally simple synthetic methods for 1,2-aminoalcohols via electroreductive cross aza-pinacol coupling between N-acyl diarylketimines and aldehydes. Preliminary mechanistic studies including cyclic voltammetry and density functional theory (DFT) calculations suggest that the reaction is instigated by selective electrochemical single electron transfer (SET) of N-acylketimines. The developed electrochemical protocol is compatible to biorelevant functional groups, enabling late-stage functionalization of pharmacophores.
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