Inorganic Chemistry

Electrochemically Driven Desaturation of Carbonyl Compounds


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 reaction pathway.

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Supplementary material

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Supporting Information