Electrochemically Driven Desaturation of Carbonyl Compounds
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Electrochemical techniques have long been heralded for their innate sustainability as efficient methods for
achieving redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to
unlock adjacent reactivity. To date, the most reliable methods
for achieving it have relied on transition metals (Pd/Cu) or stoichiometric reagents based on I, Br, Se, or S. Herein we report an
operationally simple pathway to such structures from enol
silanes and phosphates using electrons as the primary reagent.
This electrochemically driven desaturation exhibits a broad
scope across an array of carbonyl derivatives, is easily scalable
(1-100g), and can be predictably implemented into synthetic
pathways using experimentally or computationally derived
NMR shifts. Mechanistic interrogation suggests a radical-based