Pseudo High-Throughput Development and Optimization of the Electrochemical Oxidation of Sensitive Propargylic Benzylic Alco-hols

23 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. The ther-mal oxidation of propargylic benzylic alcohols presents an acute challenge in the synthesis of complex molecules and various traditional oxidation methods proceed with low efficiency or not at all. We describe the convenient preparation and charac-terization of N-hydroxytetrafluorophthalimide (TFNHPI) and a practical, green electrochemical oxidation protocol that em-ploys TFNHPI as a stable, efficient electrochemical mediator. The electrochemical method employing TFNHPI to oxidize propargylic benzylic alcohols was developed and optimized in pseudo high-throughput fashion using a bank of inexpensive two-electrode power supplies. The electrochemical oxidation of propargylic benzylic alcohol was also leveraged to develop efficient synthetic pathways to prepare gram quantities of resveratrol natural products such as the pauciflorols.


Natural Products
Redox Mediator

Supplementary materials

Supporting Information
Detailed experimental procedures, photographs of experi-mental apparatus, characterization data for all compounds, cyclic voltammograms, and X-ray crystallographic data.


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