Intramolecular reductive cyclisations using electrochemistry: development of environmentally friendly synthetic methodologies

Duñach, Élisabet; Medeiros, Maria José; Olivero, Sandra

doi:10.1039/b608228a

Cited by 38 publications

(24 citation statements)

References 184 publications

(141 reference statements)

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“…Cathodic reductions, including transition metal catalyzed reactions of organic halides with subsequent intermolecular and intramolecular addition to C-C double and C-C triple bonds, to aromatic systems, carbonyl groups and epoxides have been summarized in a review [51].…”

Section: Activated C-c Double Bonds and Organic Halidesmentioning

confidence: 99%

Contributions of organic electrosynthesis to green chemistry

Schäfer

2011

Comptes Rendus. Chimie

240

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Section: Activated C-c Double Bonds and Organic Halidesmentioning

confidence: 99%

Contributions of organic electrosynthesis to green chemistry

Schäfer

2011

Comptes Rendus. Chimie

240

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“…This type of coupling process has received considerable attention and has been reviewed from time to time [1][2][3]. Mechanistic investigations have been carried out to understand the highly selective hydrodimerisation even in the aqueous medium in the presence of surfactants [4,5].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical homolytic and heterolytic coupling of activated olefins in the absence and presence of benzyl bromide in microemulsion

2008

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Electrochemical reduction of four activated olefins namely cyclohexenone (CH), cyclopentenone (CP), methylmethacrylate (MMA), acrylonitrile (AN) in the absence and presence of benzylbromide (BBr) were investigated in CTAB/n-hexane/n-butanol/water based bicontinuous microemulsion (lE). Both cyclic voltammetric studies and galvanostatic preparative electrolysis were carried out. Cyclic voltammetric results in lE were also compared with those in N,N-dimehtylformamide (DMF) medium. Adsorption effects are observed both in DMF and lE. AN undergoes one electron reduction in aprotic solvent and two electron reduction in lE. CH, CP, BBr undergo one electron reduction and yield significant homolytic coupled products under galvanostatic conditions. AN and MMA lead to two electron reduction under identical conditions. In the presence of BBr, CH and CP alone yield significant heterolytic coupled products with simultaneous competitive resin formation. Reduction of AN leads to the formation of a identifiable quantity of propylamine and 3-phenylpropylamine in the absence and in the presence of BBr, respectively.

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“…Pd(II), Ni(II) or Co(II) coordination complexes have been reported as mediators of this process (Scheme 10). 66,73 The reduced form of these complexes can be produced as the first step in the reaction. These species were shown to react further with organic halides to form reactive organometallic species that lead to productive chemistry.…”

Section: Reductive Dehalogenations and Related Reactionsmentioning

confidence: 99%

Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry

et al. 2015

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The present review surveys current chemical understanding of catalysis by addition and removal of an electron. As an overarching theme of this type of catalysis, we introduce the role of redox scales in oxidation and reduction reactions as a direct analogue of pK a scales in acid/base catalysis. Each scale is helpful in determining the type of reactivity to be expected. In addition, we describe several means of generating electrons and holes via chemical reactions, plasmonic resonance, radiolytic, photochemical and electrochemical methods. We specifically draw parallels between the now well-established fields of photoredox catalysis and chemical opportunities made available by electrochemical methods. We highlight accessible potential ranges for a series of electrochemical solvents and provide a discussion on experimental design, pitfalls and some remaining challenges in preparative organic electrochemistry.

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Intramolecular reductive cyclisations using electrochemistry: development of environmentally friendly synthetic methodologies

Cited by 38 publications

References 184 publications

Contributions of organic electrosynthesis to green chemistry

Contributions of organic electrosynthesis to green chemistry

Electrochemical homolytic and heterolytic coupling of activated olefins in the absence and presence of benzyl bromide in microemulsion

Catalysis by electrons and holes: formal potential scales and preparative organic electrochemistry

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