The green and convergent paired Diels–Alder electro-synthetic reaction of 1,4-hydroquinone with 1,2-bis(bromomethyl)benzene

Habibi, Davood; Pakravan, Narges; Nematollahi, Davood

doi:10.1016/j.elecom.2014.09.018

Cited by 20 publications

(19 citation statements)

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“…910 Anodic oxidation of alcohols and tin-mediated cathodic reduction of nitrate have also been combined in an undivided cell, providing oximes directly from alcohols (Figure 52F). 911 …”

Section: Paired Electrolysismentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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“…910 Anodic oxidation of alcohols and tin-mediated cathodic reduction of nitrate have also been combined in an undivided cell, providing oximes directly from alcohols (Figure 52F). 911 …”

Section: Paired Electrolysismentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

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“…Initially, compound 164, as a water-soluble precursor for the QDM 167, and maleimide 165, a water-soluble dienophile/redox catalyst were reacted. The effect of solvent on the stereochemistry of the DÀ A reaction was studied [70] and it was found that in aqueous media the formation endo product is favored. Interestingly, under electrogenerated method the formation of endo adducts also prevailed in DMF.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

“…Likewise, it is not likely to confirm this mechanism for aqueous solution since the reduction of maleimide and N-methylmaleimide at least up to 100 V/s, is irreversible representing fast dimerisation of the radical-anions. Nevertheless, the dimerisation of Nmethylmaleimide radical-anion is relatively exhibit in DMF [70] Compounds 96 and 146 were individually oxidized and reduced via the green electrosynthesis method. The outcome demonstrated that the dienophile obtained from the oxidation of 96 contributes in two consecutive DÀ A cycloaddition with cathodically provided o-quinodimethane 147 to give 5,5a,6a,7,12,12a,13a,14-octahydropentacene-6,13dione 177 as a target product with excellent yield, selectivity, purity, with no by-product of waste were detected.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

“…In the next stage, intermediate 178 as a dienophile was treated with 147 that obtained from the reduction of 146, resulted into the corresponding product 177 (Scheme 45). [70] In 2015, Nematollahi et al accomplished and reported the electrogenerated reduction of 1,2-bis(bromomethyl)benzene 146 and examined naphthoquinones 179 a-c in ethanol/ litiumperchlorate solution using cyclic voltammetry and constant current electrolysis. [72] The voltammetric results demonstrated that a DÀ A cycloadduct reaction sequence resulted in electroreduction between 179 a-c and provided oquinodimethane 147 cathodically to afford the desired products, 180 a-c.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

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Electrochemically Induced Diels‐Alder Reaction: An Overview

Heravi

Zadsirjan

Kouhestanian

et al. 2019

The Chemical Record

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One of the most important name reactions in organic chemistry, is the Diels-Alder cycloaddition reaction. It is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile to construct a substituted cyclohexene derivative. It is the stereotypical example of a pericyclic reaction with a concerted mechanism. In synthesis, the use of electricity instead of stoichiometric amounts of oxidant or reducing agents is definitely appealing for economic, ecological and selective, reasons. In this review, we try to underscore the combination of the electrosynthesis with Diels-Alder cycloaddition reaction to establish of a powerful synthetic tool which may encourage synthetic organic chemists to use it in the future. Wiley Online LibraryScheme 6. A suggested mechanism of DÀ A reaction of electrogenerated quinones and dienes on the PTFE-fibers. Scheme 7. Electro-oxidation of Eugenol 77. P e r s o n a l A c c o u n t Wiley Online Library 286 Scheme 37. Anodic oxidation reaction of the 2-methoxy analogue 143 j and in situ trapping of the o-quinone heterodyne using enamine 144 a. Scheme 38. The synthesis of 145 e, 145 k-q using electro-oxidation pyrogallol derivatives with the enamine dienophiles. Scheme 48. The electrolysis of a 1 : 2 mixture of 3-buten-2-one ethylene acetal 183 a and cyclopentadiene 1 at 15 V for 0.2 F/mol using platinum electrodes in CH 2 C1 2 comprising LiC1O 4 /Bu 4 NC1O 4 as catalyst. Scheme 64. Regiospecific IEDDA reaction of enamine dienophile with o-azaquinone diene 232 ox , electrogenerated concurrently, to afford polyfunctionalized 1,4benzoxazine derivatives.

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“…In conventional electroorganic synthesis, the synthesis of the desired products is done either by the anodic or by the cathodic reaction and so; the reaction product at the counter electrode is undesirable. The simultaneous use of both oxidation and reduction reactions to synthesis of a product is the dream of an organic electrochemist and is a wonderful strategy [24][25][26][27][28] . At ideal conditions, a 200% current efficiency is achievable for paired electrosynthesis when both anodic and cathodic reactions to provide the similar product (convergent strategy) 15 .…”

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confidence: 99%

New insights into the electrochemical behavior of acid orange 7: Convergent paired electrochemical synthesis of new aminonaphthol derivatives

Nematollahi¹,

Momeni²

2017

Protocol Exchange

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Electrochemical behavior of acid orange 7 has been exhaustively studied in aqueous solutions with different pH values, using cyclic voltammetry and constant current coulometry. This study has provided new insights into the mechanistic details, pH dependence and intermediate structure of both electrochemical oxidation and reduction of acid orange 7. Surprisingly, the results indicate that a same redox couple (1-iminonaphthalen-2(1H)-one/1-aminonaphthalen-2-ol) is formed from both oxidation and reduction of acid orange 7. Also, an additional purpose of this work is electrochemical synthesis of three new derivatives of 1-amino-4-(phenylsulfonyl)naphthalen-2-ol (3a-3c) under constant current electrolysis via electrochemical oxidation (and reduction) of acid orange 7 in the presence of arylsulfinic acids as nucleophiles. The results indicate that the electrogenerated 1-iminonaphthalen-2(1 H)-one participates in Michael addition reaction with arylsulfinic acids to form the 1-amino-3-(phenylsulfonyl) naphthalen-2-ol derivatives. The synthesis was carried out in an undivided cell equipped with carbon rods as an anode and cathode.

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The green and convergent paired Diels–Alder electro-synthetic reaction of 1,4-hydroquinone with 1,2-bis(bromomethyl)benzene

Cited by 20 publications

References 43 publications

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Electrochemically Induced Diels‐Alder Reaction: An Overview

New insights into the electrochemical behavior of acid orange 7: Convergent paired electrochemical synthesis of new aminonaphthol derivatives

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