Indirect electrochemical oxidation of piperidin-4-ones mediated by sodium halide-base system

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…The iodide mediated α-oxidation of aryl ketones has also found applications to cleave the β-O-4 lignin model compounds . Aryl ketones could also be elaborated into α-hydroxy ketals using a NaI/NaOH system under electrolysis (Figure B). − In a similar vein, Zeng, Little, and co-workers developed an electrosynthesis of 3-amino-2-thiocyanato-α,β-unsaturated carbonyl derivatives through a bromide mediated α-oxidation of 1,3-dicarbonyls where the amino and thiocyanato moieties either originate from a single reagent or a combination of ammonium acetate and potassium isocyanate (Figure C) . Similarly, Yuan and co-workers reported an iodide mediated electrosynthesis of β-keto sulfones .…”

Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids

“…In the present work, we decided on a more challenging task of electrochemically induced intermolecular cross-dehydrogenative C–O coupling of β-dicarbonyl compounds with carboxylic acids with high yields at CCE in an undivided cell (Scheme , c). Despite the fact that many processes of anodic nature, ,− such as hydroxylation, − halogenation, dimerization, and cathodic nature, for example, carbonyl group reduction, − can take place in similar systems (Scheme , a), an acyloxy-product is selectively formed under our conditions.…”

Electrochemical strategies for C–H functionalization and C–N bond formation

“…408 The iodide-mediated oxidation system was subsequently employed for a-hydroxylation of cyclohexanones 409 and piperidin-4-ones. 410 Bromide-mediated a-oxidation has also been used for accessing spiro-dihydrofuran derivatives from dimedone and aldehydes (Scheme 38). 411 Furthermore, both intermolecular 412 and intramolecular [413][414][415][416][417][418][419][420][421][422][423][424][425][426][427][428] protocols for C-C bond formation based on halide-mediated anodic oxidation of carbonyl compounds and related derivatives have also been disclosed.…”