Direct electrosynthesis of a series of novel caffeic acid analogues through a clean and serendipitous domino oxidation/thia-Michael reaction

Alizadeh, Abdolhamid; Khodaei, Mohammad Mehdi; Fakhari, Mitra; Shamsuddin, Mustaffa

doi:10.1039/c4ra02046d

Cited by 10 publications

(4 citation statements)

References 44 publications

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“…The accuracy of these suggestion could be simply proved by comparing the calculated [24] and experimentally obtained 1 HNMR data of the possible structures [25,26] (Table 2). For instance, 1 HNMR investigation of the product obtained from 1b ?…”

Section: Resultsmentioning

confidence: 95%

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

et al. 2014

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A series of novel polycyclic structures, with an imidazothiazole central core, were successfully synthesized through the anodic oxidation of catechols in the presence of 2-imidazolidine thione, as nucleophiles in aqueous solution. The cyclic voltammetric results indicated that one-pot multi-step sequential reactions occur between the electrochemically derived o-benzoquinones intermediates and nucleophiles affording fused polyheterocyclic compounds. The mechanism of these catalyst-free, tandem reactions are proved as ECECE or ECECCE pathways using potentiostatic and galvanostatic coulometries. In addition, the electrosyntheses of fused imidazo[2,1-b]thiazoles have been successfully performed in ambient conditions in an undivided cell using an environmentally friendly method with high atom economy and current efficiency. The novel fused polyheterocycles were fully characterized by FT-IR, 1 H NMR, 13 C NMR, and HR-MS spectrometric methods.

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Section: Resultsmentioning

confidence: 95%

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

et al. 2014

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“…Finally, the cross‐coupling of radical A and C could furnish the desired product 3 ab (Path A). In addition, another mechanism approach that cannot be ignored involves anodic oxidation of hydroquinone to form benzoquinone followed by Michel addition with 2 b to obtain the final product 3 ab (Path B) [11e,h,i,12] …”

Section: Methodsmentioning

confidence: 99%

Electrochemical‐In‐Situ‐Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones

et al. 2021

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The electrochemical in-situ oxidative sulfonylation of phenols with sulfinic acids access to sulfonylated hydroquinones has been developed. A series of sulfonylated hydroquinones were prepared under mild mediator-, catalyst-and exogenous-oxidant-free conditions. Notably, such an electrochemical in-situ-oxidative synthetic strategy presented wide functional group tolerance and amenability to gram-scale synthesis with 62-80% yields.

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“…[675][676][677][678][679][680][681] Considering their relatively low oxidation potentials, it is perhaps unsurprising that an assortment of nucleophiles are compatible with these processes without being subjected to oxidation. Here, amines, [682][683][684][685][686][687][688][689] azide, 690,691 enolates and other carbon nucleophiles, [692][693][694][695][696][697][698][699][700][701][702][703][704][705][706][707][708][709][710][711] nitrate, 712 sulfinates [713][714][715][716][717][718][719][720][721][722][723]…”

Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

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

2018

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Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Direct electrosynthesis of a series of novel caffeic acid analogues through a clean and serendipitous domino oxidation/thia-Michael reaction

Cited by 10 publications

References 44 publications

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

Electro-generated ortho-quinoide intermediates: templates for feasible construction of a series of novel imidazo[2,1-b]thiazole derivatives through one-pot five-step domino hetero-annulation process

Electrochemical‐In‐Situ‐Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones

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

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