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.
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.
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