Year: 2022
Type: article
Abstract: 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.
Source: Organic Letters
Institution: University of Delaware
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Funders: National Science Foundation, U.S. Department of Energy, University of Delaware, National Institutes of Health, Office of Science, National Institute of General Medical Sciences, National Center for Research Resources, Division of Chemistry, Basic Energy Sciences, Office of Experimental Program to Stimulate Competitive Research
Awards: NEW; TITLE: DEVELOPMENT OF A DUAL MODALITY TOMOGRAPHIC IMAGING SYSTEM, FOR BIOLUMINESCENCE AND PET; PI: ARION CHATZIIOANNOU, G2902092823, Discovery of Chemical Probes and Therapeutic Leads, Phase II, G335888736, G4040836280, CRIF:MU Cryprobe Upgrade of a NMR Spectrometer, G501384772, PROBING THE SUSTAINABLE REDUCTION OF CO2, N2 AND NO3– TO FUELS AND CHEMICALS USING NON-TRADITIONAL PORPHYRINOID CATALYSTS, G545157245, G566787721, G5679962385, Acquisition of a 400 MHz NMR Spectrometer, High Performance Digital NMR Spectrometer, Acquisition of a Single-Crystal X-ray Diffractometer, Molecular Design of Advanced Biomaterials, High Sensitivity NMR Spectrometer with Cryoprobe, MRI: Acquisition of a High Resolution Mass Spectrometer for Small Molecule Analysis, G9000004818, G9000217648, Q-Exactive Orbitrap LC-MC/MS System
OpenAlex ID: W4212851992