Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols
Chad E Hatch1, Maxwell I Martin1, Philip H Gilmartin1
1Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Abstract:
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.
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