Electrochemically induced Diels–Alder reaction of p-benzoquinone with 1,3-cyclopentadiene

Nematollahi, Davood; Ghorbani, Adel

doi:10.1016/j.jelechem.2008.07.033

Cited by 11 publications

(11 citation statements)

References 28 publications

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“…In the pursuit of this goal, a range of different benzofurans (291 and 293) have been accessed using 1,3-diketones, [745][746][747][748][749][750][751][752][753][754][755][756] a-cyanoketones 757 774 derivatives. Furthermore, the electrochemically generated benzoquinone derivatives can also engage in [4+2] cycloaddition in the presence of cyclopentadiene, 775,776 produce trimerization products [777][778][779] or engage in transfer hydrogenation catalysis. [780][781][782] A dual electro-and organocatalysis strategy was outlined by Jørgensen and coworkers, which enabled the enantioselective intermolecular a-arylation of aldehydes.…”

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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Section: Electrochemical Oxidative Cross-couplingsmentioning

confidence: 99%

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

2018

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“…In 2008 the electrochemical oxidation reaction of 1,4hydroquinone 96 using 1,3-cyclopentadiene 1 as the diene in H 2 O/EtOH (40/60) by cyclic voltammetry and controlledpotential coulometry strategy at 0.70 V versus SCE was achieved and reported by Nematollahi and Ghorbani. [39] The outcomes disclosed that the dienophile obtained by oxidation of hydroquinone participates underwent two sequential DÀ A reactions with cyclopentadiene and through a route transforms into the 1,4,4a,5,8,8a,9a,10a-octahydro-(1,4), (5,8)-dimethano-9,10-anthraquinone 98 in a moderate yield. In this strategy a simple cell with no toxic reagents at the carbon electrode was used.…”

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%

“…The thiol compounds were synthesized via reaction of isocyanate-bearing compounds with hydroquinone. The electrogenerated thiol was assorted with 11-mercaptoundecanol [HS(CH 2 ) 11 OH] to give a mixture of monolayer. Notably, cyclic voltammetry was applied for the description of the release actions (Scheme 25).…”

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%

“…During the years, several books, reports and reviews have repeatedly praised the diversity of electrosynthesis for the preparation of organic compounds, both in the academia as well as in industry. [11] Among various electrochemical methods, [12] the paired electrosynthesis particularly the convergent strategy has been found being more efficient and powerful than other strategies. [13] One of interesting feature of an electrochemical reaction is the construction of the same product from the same starting materials on the anode and cathode processes.…”

Section: Introductionmentioning

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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“…Many organic compounds are unstable after oxidation and show a tendency to participate in secondary reactions such as degradation, 1,2 reaction with the solvent, 3 dimerization 4,5 and reaction with nucleophiles [6][7][8][9][10] or other reactive molecules. [11][12][13] For the chemistry described herein, the mechanism and the optimal reaction conditions for achieving the desired product were determined using voltammetric methods such as cyclic voltammetry (a method with short time window) and controlled-potential coulometry (a method with long time window).…”

mentioning

confidence: 99%

Direct Electrochemical Dimerization of N,N′-Diphenylbenzidine

Shahparast¹,

Nematollahi²,

Sharafi‐Kolkeshvandi³

et al. 2019

J. Electrochem. Soc.

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Electrochemical dimerization of N,N -diphenylbenzidine (DFB) has been studied in a water/DMF (20/80, v/v) mixture by cyclic voltammetry and controlled potential techniques. The data obtained show that anodically generated N 4 ,N 4 -diphenyl-[1,1bi(cyclohexylidene)]-2,2 ,5,5 -tetraene-4,4 -diimine (DFB ox ) reacts with the parent molecule to form a dimer of DFB. The efficient electrochemical synthesis of DFB dimer was successfully carried out under constant current conditions in an undivided cell using carbon anode and stainless steel cathode in water/DMF (20/80, v/v) mixture. The voltammetric and computational data show that the oxidation of dimer is easier than that of monomer (DFB).

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Electrochemically induced Diels–Alder reaction of p-benzoquinone with 1,3-cyclopentadiene

Cited by 11 publications

References 28 publications

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

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

Electrochemically Induced Diels‐Alder Reaction: An Overview

Direct Electrochemical Dimerization of N,N′-Diphenylbenzidine

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