Paired electrochemical conversion of nitroarenes to sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols

Mokhtari, Banafsheh; Nematollahi, Davood; Salehzadeh, Hamid

doi:10.1039/c7gc03576d

Cited by 55 publications

(41 citation statements)

References 34 publications

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“…SCE . Furthermore, also the hydroxylamine/nitroso half‐wave potentials (E 1/2 ) shift to more negative values with increasing pH …”

Section: Nitro Derivativesmentioning

confidence: 95%

“…The idea of synthesizing N ‐sulfonylated phenylhydroxylamines (Scheme , 5c ) was expanded and improved some years later by the group of Nematollahi. They mixed nitrobenzene derivatives ( 5a ) and sodium salts of arylsulfinic acids ( 5b ) during the electrolysis and carried out the reduction also under constant current conditions . Different types of N ‐sulfonated phenylhydroxylamines, but also sulfonamides ( 5d ) and arylsulfones ( 5e ) were obtained, depending on the nature of the starting nitro compound and its substitution pattern as displayed in Scheme .…”

Section: Nitro Derivativesmentioning

confidence: 99%

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Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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In this review,t he versatile and rich chemistry for the electrochemical reductiono fs ubstrates involving N À Ob onds is surveyed. By the cathodic treatment of nitro,n itroso and other oxygenated organic nitrogen substrates,v ersatile andr eactive intermediates are formed which can be subsequently converted to high value-added products. In many examples,n itrogen heterocycles are selectively formed, but, also depending on the electrolytic conditions, free oximes,n itrones,a mines and other entities can be obtained as well. Ther ecent decades have witnessed twom ajor advances-(i)g oing directly to more complext arget molecules and (ii)c onductingt he electrolysesi nm uch simpler set-ups.Both improvements make the cathodic access of the target compoundsm uch more practical and scalable. 1I ntroduction 2N itro Derivatives 2.1 IntermolecularReactions 2.2 IntramolecularReactions:Synthesis of Heterocycles 3O ximes 4O ther Functionalities 5C onclusions

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“…SCE . Furthermore, also the hydroxylamine/nitroso half‐wave potentials (E 1/2 ) shift to more negative values with increasing pH …”

Section: Nitro Derivativesmentioning

confidence: 95%

Section: Nitro Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

2020

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“…Paired electrolysis has received a great deal of attention recently . This technology allows both electrocatalytic oxidation (ECO) and electrocatalytic hydrogenation (ECH) to occur through adsorbed oxygen ( O ads ) or adsorbed hydrogen ( H ads ) species, respectively.…”

Section: Introductionmentioning

confidence: 99%

Biomass Valorization via Paired Electrosynthesis Over Vanadium Nitride‐Based Electrocatalysts

Sun

Yao

et al. 2019

Adv Funct Materials

151

124

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Paired electrosynthesis is a promising technology with the potential to generate value-added products at both electrodes in a cost-effective manner. Herein, 3D vanadium nitride (VN) and Pd/VN hollow nanospheres are successfully fabricated and coupled to carry out simultaneous electrocatalytic oxidation (ECO) and electrocatalytic hydrogenation (ECH) of 5-hydroxymethylfurfural (HMF) into 2, 5-furandicarboxylic acid (FDCA) and 2,5-bishydroxymethyl-tetrahydrofuran (DHMTHF), respectively. VN shows excellent ECO performance with high HMF conversion (≥98%), FDCA selectivity (≥96%), and faradaic efficiency (≥84%) after a stability test, and Pd/VN achieves high ECH selectivity for DHMTHF at ≥88% and an HMF conversion of ≥90%, with a faradaic efficiency of ≥86%. VN and Pd/VN incorporated into a membrane electrode assembly in a paired electrolysis system shows potential for large-scale biomass conversion and upgrading. Theoretical calculations reveal that the higher performance of VN for the production of ECO can be attributed to its lower d-band center level relative to the Fermi level compared to that of V 2 O 5 , which favors HMF chemisorption and activation. This study paves the way for developing paired electrosynthesis technologies with the potential for biomass utilization and energy conversion.

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“…In 2018, Nematollahi and co‐workers reported a paired electrochemical method for the synthesis of sulfonamides, diarylsulfones, and bis(arylsulfonyl)aminophenols by using nitrobenzene derivatives and arylsulfinic acids as starting materials (Scheme ) . For the electrochemical oxidation of nitrobenzene, p ‐nitroaniline, and p ‐nitrophenol in the presence of arylsulfinic acids, the products were sulfonamides, diarylsulfones, and bis(arylsulfonyl)aminophenols, respectively.…”

Section: C−s Bond Formation or S−x (X=n O S Se) Bond Formation Thrmentioning

confidence: 99%

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

Hong

Xiao

et al. 2020

ChemSusChem

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The electrolysis of organic acids has garnered increasing attention in recent years. In addition to the famous electrochemical decarboxylation known as Kolbe electrolysis, a number of other electrochemical processes have been recently established that allow for the construction of carbon–heteroatom and sulfur–heteroatom bonds from organic acids. Herein, recent advances in electrochemical C−X and S−X (X=N, O, S, Se) bond‐forming reactions from five classes of organic acids and their conjugate bases, namely, carboxylic, thiocarboxylic, phosphonic, sulfinic, and sulfonic acids, are surveyed.

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Paired electrochemical conversion of nitroarenes to sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols

Abstract: A paired electrochemical synthesis of sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols using nitrobenzene derivatives and arylsulfinic acids as starting materials under green conditions.

Cited by 55 publications

References 34 publications

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Recent Advances in the Electrochemical Reduction of Substrates Involving N−O Bonds

Biomass Valorization via Paired Electrosynthesis Over Vanadium Nitride‐Based Electrocatalysts

Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation

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