Journal
NATURE CHEMISTRY
Volume 13, Issue 4, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41557-021-00640-2
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Funding
- NIH [GM-118176]
- NSF [1740656]
- AGC Inc.
- Council for Higher Education
- Fulbright Israel
- Yad Hanadiv
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1740656] Funding Source: National Science Foundation
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This new electrochemical method utilizes electrons as the primary reagent to efficiently achieve carbonyl desaturation from enol silanes and phosphates, demonstrating a broad scope of applicability and scalability.
Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access 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 (1-100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway.
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