Product diversity by changing the electrode potential. Synthesis, kinetic evaluation and antibacterial activity of arylsulfonyl-4,4'-biphenol and bis-arylsulfonyl-4,4'-biphenol derivatives

Nematollahi, Davood; Baniardalan, Maryam; Khazalpour, Sadegh; Pajohi‐Alamoti, Mohammadreza

doi:10.1016/j.electacta.2015.12.230

Cited by 18 publications

(11 citation statements)

References 40 publications

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“…All of these results are in agreement with the participation of electrogenerated MQI in the Michael addition reaction with BS [28][29][30][31][32][33][34] . Fig.…”

Section: Resultssupporting

confidence: 83%

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

Nematollahi

Khazalpour

Ranjbar

et al. 2017

Sci Rep

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This is one of the few examples in which the diverse products have been synthesized just by changing the applied potential. The synthesis of sulfonyl derivatives of p-methylaminophenol were carried out by reaction of the electrogenerated p-methylquinoneimine with sulfinic acids. Various types of mono (MSP), bis (BSP) and tris (TSP) sulfonyl p-methyl aminophenols were obtained by changing the electrode potential, in one pot under green conditions. The mono sulfonyl-p-(methylamino)phenol derivatives (MSP) were assessed for their in vitro antibacterial activity against the gram positive (Staphylococcus aureus) and gram negative (Escherichia coli) strains. It was found that the tested compounds were more active against Staphylococcus aureus than Escherichia coli. We also found that the antimicrobial activity of MSP derivatives to vary in the order MSP4 (R = CH3) > MSP1 (R = p-tolyl) ≈ MSP2 (R = phenyl) > MSP3 (R = p-ClC6H4). Moreover, the observed homogeneous rate constants (k obs) of the reaction of p-methyl quinoneimine with sulfinic acids were estimated in various pH values, based on the EC and ECEC mechanisms, by comparing the simulated cyclic voltammograms with the experimental ones.

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“…All of these results are in agreement with the participation of electrogenerated MQI in the Michael addition reaction with BS [28][29][30][31][32][33][34] . Fig.…”

Section: Resultssupporting

confidence: 83%

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

Nematollahi

Khazalpour

Ranjbar

et al. 2017

Sci Rep

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“…In 2016, Nematollahi and co‐workers reported the electrochemical synthesis of arylsulfonyl‐4,4′‐biphenol and bis‐phenylsulfonyl‐4,4′‐biphenol derivatives through the electrochemical oxidation of 4,4′‐biphenol in the presence of arylsulfinic acids as nucleophiles (Scheme ) . Different products can be obtained, depending on the electrode potential.…”

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

confidence: 96%

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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“…In 2015, Yuan and co‐workers developed a electrochemical oxidative sulfonylation of olefins with sodium sulfinates. Soon after, Waldvogel, Yu and Nematollahi– reported related works, respectively. Considering the significance of this type of reaction, we conceived that C−H sulfonylation of anilines could be achieved via an electrochemical oxidative C−S bond formation.…”

Section: Figurementioning

confidence: 99%

Electrochemical Oxidative C−H Sulfonylation of Anilines

Wang

et al. 2019

Asian J Org Chem

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Product diversity by changing the electrode potential. Synthesis, kinetic evaluation and antibacterial activity of arylsulfonyl-4,4'-biphenol and bis-arylsulfonyl-4,4'-biphenol derivatives

Cited by 18 publications

References 40 publications

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility

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

Electrochemical Oxidative C−H Sulfonylation of Anilines

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