Substrate‐Dependent Electrochemical Dimethoxylation of Olefins

Zhang, Sheng; Li, Lijun; Wu, Ping; Gong, Pengtao; Li, Rui; Xu, Kun

doi:10.1002/adsc.201801173

Cited by 42 publications

(24 citation statements)

References 41 publications

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“…5,6 The moving contact line in a LLS system is determined not only by the interactions among the liquid molecules but also by the interactions between the liquid molecules 7 and the solid materials. [8][9][10][11] Thus, the movement of the contact line is affected by the liquid properties, the solid properties and their surface structures. 12,13 It is generally accepted that the moving contact line is controlled by the unbalanced force and the energy dissipation near the contact line.…”

Section: Introductionmentioning

confidence: 99%

Moving mechanisms of the three-phase contact line in a water–decane–silica system

et al. 2019

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The movement of the three-phase contact line with chain molecules in the liquid phase displays more complex mechanisms compared to those in the usual liquid-liquid-solid systems and even to the gasliquid-solid systems controlled by the traditional single-molecule adsorption-desorption mechanisms.By introducing decane molecules with chain structures, we demonstrate from molecular dynamics insights that the moving mechanism of the contact line in a water-decane-silica system is totally different from traditional mechanisms. Three different wettability-related moving mechanisms including "Roll up", "Piston" and "Shear" are revealed corresponding to the hydrophilic, intermediate and hydrophobic three-phase wettability, respectively. In the "Roll up" mechanism, the decane molecules are rolled up by the competitively adsorbed water molecules and then move forward under the driving force; when the "Piston" mechanism happens, the decane molecules are pushed by the piston-like water phase owing to the comparable adsorption interactions of the two liquids on the solid surface; in the "Shear" mechanism, the contact line is hard to drive due to the stronger decane-silica interactions but the decane molecules far away from the solid surface will move forward. Besides, the time-averaged velocity of the moving contact line is greatly related to the moving mechanisms. For the "Roll up" mechanism, the contact line velocity increases first and then reaches a steady value; for the "Piston" mechanism, the contact line velocity has a maximum value at the start-up stage and then decreases to a stable value; for the "Shear" mechanism, the contact line velocity fluctuates around zero due to the thermal fluctuation of the molecules. Additionally, the mean distance from Molecular Kinetics Theory increases with decreasing hydrophilicity and the displacement frequency in "Roll up" mechanism is 2 orders of magnitude higher than that in the "Piston" mechanism, further demonstrating the different moving mechanisms from a quantitative point of view. Fig. 7 MKT parameters. (a) Velocity plotted in logarithmic scale versus cos q d . (b) Parameters l and K 0 of the MKT at different three-phase wettabilities and the comparison with other works.This journal is

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Section: Introductionmentioning

confidence: 99%

Moving mechanisms of the three-phase contact line in a water–decane–silica system

et al. 2019

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“…[2] The related electrochemical dearomative 1,2-difunctionalization of (hetero)arenes and in particular indoles has been less studied. [3][4][5][6][7][8] The dearomatization of indole, for which we have been interested for almost a decade, [9,10] generates three dimensional indolines of potential biological relevance. [11] In few cases, dearomative electrolysis could be performed from an NÀ H indole substrate [6] as it was demonstrated by Harran during the 60 gram-scale synthesis of the benzofuroindoline core of DZ-2384, a highly potent antitumoral agent inspired by the natural product diazonamide A.…”

Section: Tion; Dihydroxylation; Electrocatalystmentioning

confidence: 99%

“…[6b] However, most electrochemical methods to achieve this transformation rely on the generation of a radical cation A via the direct anodic oxidation of the indole nucleus 1 bearing an electronwithdrawing group on the nitrogen to deliver indolines 2. [7,8] According to this concept, Royer reported, in 2004, one example of the dearomative dimethoxylation of a β-tetrahydrocarboline. [7a] One example of the dimethoxylation of the 2,3-unsubstituted NÀ Ts indole was latter reported by Zhang and Xu.…”

Section: Tion; Dihydroxylation; Electrocatalystmentioning

confidence: 99%

Electrochemical Dearomative Dihydroxylation and Hydroxycyclization of Indoles

Guillot

Kouklovsky

et al. 2020

Adv Synth Catal

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“…Using a similar strategy to that reported by Moeller and co‐workers, in 2019, Xu and co‐workers reported lactone formation from carboxylic acid containing styrene substrates (Scheme ) . The endo ‐type cyclization in this work deserves attention.…”

Section: Ester C−o Bond Formation Through Electrolysis Of Carboxylic mentioning

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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Substrate‐Dependent Electrochemical Dimethoxylation of Olefins

Cited by 42 publications

References 41 publications

Moving mechanisms of the three-phase contact line in a water–decane–silica system

Moving mechanisms of the three-phase contact line in a water–decane–silica system

Electrochemical Dearomative Dihydroxylation and Hydroxycyclization of Indoles

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

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