Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.
Chad E HatchMaxwell I MartinPhilip H GilmartinLu XiongDanielle J BeamGlenn P A YapMatthew J Von BargenJoel RosenthalWilliam J ChainPublished in: Organic letters (2022)
The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. We describe the preparation and characterization of N -hydroxytetrafluorophthalimide (TFNHPI) and pseudo-high-throughput development of a green electrochemical oxidation protocol for sensitive propargylic benzylic alcohols that employs TFNHPI as a stable electrochemical mediator. The electrochemical oxidation of propargylic benzylic alcohols was leveraged to develop short synthetic pathways for preparing gram quantities of resveratrol natural products such as pauciflorols.