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.
Electrochemical techniques have helped to enable the total synthesis of natural products since the pioneering work of Kolbe in the mid 1800’s. The electrochemical toolset grows every day and these new possibilities change the way chemists look at and think about natural products. This review provides a perspective on total syntheses wherein electrochemical techniques enabled the carbon‐carbon bond formations in the skeletal assembly of important natural products, discussion of mechanistic details, and representative examples of the bond formations enabled over the last several decades. These bond formations are often distinctly different from those possible with conventional chemistries and allow assemblies complementary to other techniques.
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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