Coupure cathodique de liaisons carbone-oxygene—III Reduction de pinacols sur electrode de mercure—une possibilite de rupture electrochimique de liaisons carbone-carbone

Michel, Marie-Andrée; Mousset, G.; Simonet, Jacques; Lund, Henning

doi:10.1016/0013-4686(75)90051-1

Cited by 26 publications

(9 citation statements)

References 9 publications

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“… [26] Similarly, Lund and co‐workers demonstrated the electrochemical reduction of an extensive scope of π‐activated alcohols under similar electroreductive conditions in the 1970s (Figure 3 ). [ 8 , 27 ] For some of the unsaturated substrates, alkenes or alkynes were reduced prior to C−O bond cleavage, furnishing saturated alcohols alongside the deoxygenation products, while pinacols were shown to undergo either C−C and/or C−O bond cleavage, depending on the used additive. Electroreduction of a series of unsaturated alcohols was further demonstrated by Lund and Lund in 1984.…”

Section: Electrochemical C−o Bond Activation In Unfunctionalized Alco...mentioning

confidence: 99%

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

et al. 2022

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Alcohols and their derivatives are ubiquitous and versatile motifs in organic synthesis. Deoxygenative transformations of these compounds are often challenging due to the thermodynamic penalty associated with the cleavage of the CÀ O bond. However, electrochemically driven redox events have been shown to facilitate the CÀ O bond cleavage in alcohols and their derivatives either through direct electron transfer or through the use of electron transfer mediators and electroactive catalysts. Herein, a comprehensive overview of preparative electrochemically mediated protocols for CÀ O bond activation and functionalization is detailed, including direct and indirect electrosynthetic methods, as well as photoelectrochemical strategies.

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Section: Electrochemical C−o Bond Activation In Unfunctionalized Alco...mentioning

confidence: 99%

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

et al. 2022

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“…[26] Similarly, Lund and co-workers demonstrated the electrochemical reduction of an extensive scope of πactivated alcohols under similar electroreductive conditions in the 1970s (Figure 3). [8,27] For some of the unsaturated substrates, alkenes or alkynes were reduced prior to CÀ O bond cleavage, furnishing saturated alcohols alongside the deoxygenation products, while pinacols were shown to undergo either CÀ C and/or CÀ O bond cleavage, depending on the used additive. Electroreduction of a series of unsaturated alcohols was further demonstrated by Lund and Lund in 1984.…”

Section: Electrochemical Cà O Bond Activation In Unfunctionalized Alc...mentioning

confidence: 99%

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

et al. 2022

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“…[251 HO-+ CHjCN ;--+ HOH + C H~C N Compte tenu des rtsultats de cette tlectrolyse, on c o n~o i t que dans l'ttape IV, les radicaux anions 26 a nouveau apparus, livrent l'oltfine 17 selon [22] a [24]. Dans cette ttape, la formation de polymkres est induite partir de 17 selon [27] et celle du nitrile 3a s'effectue probablement selon [28] (cf.…”

Section: Etape Illunclassified

Réaction entre solvant et espèces intermédiaires apparues lors de l'électroréduction–acylation de la fluorènone et de la fluorènone-anil dans l'acétonitrile

Degrand¹,

Belot²,

Compagnon³

et al. 1983

Can. J. Chem.

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The electrogenerated anions −CH2CN induce the conversion of the various reduction–acylation products of fluorènone 1a and its anil 1b in acetonitrile into 1a and 1b; this phenomenon is controlled by the fortuitous introduction of molecular oxygen. The −CH2CN anions catalyse the transformation of 1a and 1b into fluorenylideneacetonitrile (FlC=CHCN) 17, convertible into the nitriles FlC=CHC(CN)=C(NH2)CH38, FlC=C(CN)CHFl 10, and FlC=C(CN)CH2CN 11. These observations allow us to interpret the formation of the products appearing during the electrolysis of fluorenone in acetonitrile in the presence of an equivalent of chloride or anhydride of ω-chloro acid. The products of reduction–acylation appear successively, followed by the nitriles, FlC(OH)CH2CH2CN 3a, 10, FlC(OH)CH2CN 24, and polymers. Because of its basicity the fluorenone radical anion promotes reactions with the solvent, olefin 17 being a preferred intermediate. Bis-fluorenol, fluorenol, and finally fluorene are found with 1a and the above products. [Journal translation]

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Coupure cathodique de liaisons carbone-oxygene—III Reduction de pinacols sur electrode de mercure—une possibilite de rupture electrochimique de liaisons carbone-carbone

Cited by 26 publications

References 9 publications

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives

Réaction entre solvant et espèces intermédiaires apparues lors de l'électroréduction–acylation de la fluorènone et de la fluorènone-anil dans l'acétonitrile

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