Name: 5,6-Dihydro-2H-pyran-2-one. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5,6-Dihydro-2H-pyran-2-one, is researched, Molecular C5H6O2, CAS is 3393-45-1, about Electrochemically driven desaturation of carbonyl compounds. Author is Gnaim, Samer; Takahira, Yusuke; Wilke, Henrik R.; Yao, Zhen; Li, Jinjun; Delbrayelle, Dominique; Echeverria, Pierre-Georges; Vantourout, Julien C.; Baran, Phil S..
Electrochem. 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 electrochem. 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 exptl. 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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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI