Electrocatalytic reduction of benzal chloride by cobalt(I)(salen). A mechanistic investigation

Fry, Albert J.; Sirisoma, U. Nilantha

doi:10.1021/jo00070a030

Cited by 39 publications

(6 citation statements)

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“…Publications describing cobalt(I) salen-mediated reductions of simple alkyl halides and dihalides are numerous, − and there has been a comparable number of studies involving aromatic halides. ,− Rusling and co-workers investigated the use of several electrogenerated cobalt(I) complexes [cobalt(I) salen, vitamin B 12s , and cobalt(I) phthalocyanine] as catalysts, both in homogeneous phases and in bicontinuous microemulsions, for the reduction of a number of compounds, including 4,4′-(2,2,2-trichloroethane-1,1-diyl)bis(chlorobenzene) (DDT). − In our laboratory, electrogenerated cobalt(I) salen has been employed for the catalytic reductions of 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113), DDT, 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a), and hexa- and pentachlorobenzene …”

Section: Halogenated Environmental Pollutantsmentioning

confidence: 99%

Electroreductive Remediation of Halogenated Environmental Pollutants

et al. 2016

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Electrochemical reduction of halogenated organic compounds is gaining increasing attention as a strategy for the remediation of environmental pollutants. We begin this review by discussing key components (cells, electrodes, solvents, and electrolytes) in the design of a procedure for degrading a targeted pollutant, and we describe and contrast some experimental techniques used to explore and characterize the electrochemical behavior of that pollutant. Then, we describe how to probe various mechanistic features of the pertinent electrochemistry (including stepwise versus concerted carbon-halogen bond cleavage, identification of reaction intermediates, and elucidation of mechanisms). Knowing this information is vital to the successful development of a remediation procedure. Next, we outline techniques, instrumentation, and cell designs involved in scaling up a benchtop experiment to an industrial-scale system. Finally, the last and major part of this review is directed toward surveying electrochemical studies of various categories of halogenated pollutants (chlorofluorocarbons; disinfection byproducts; pesticides, fungicides, and bactericides; and flame retardants) and looking forward to future developments.

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Section: Halogenated Environmental Pollutantsmentioning

confidence: 99%

Electroreductive Remediation of Halogenated Environmental Pollutants

et al. 2016

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“…In contrast, the reduction of alkyl or aryl halides can also be catalyzed by electrogenerated cobalt(I) salen [1,[9][10][11][12], which readily undergoes a S N 2 reaction with the substrates to form the pentacoordinate organocobalt(III) salen intermediates. It has been proposed that ultraviolet-visible (UV-vis) light can photodecompose the organocobalt(III) salen complex to produce the corresponding radical and cobalt(II) salen within a solvent cage [12,13].…”

Section: Introductionmentioning

confidence: 99%

Catalytic reduction of 1- and 2-bromooctanes by a dinickel(I) Schiff base complex containing two salen units electrogenerated at carbon cathodes in dimethylformamide

Day

Silvers

2008

Journal of Electroanalytical Chemistry

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“…In the absence of ligand, the cobalt(I) species undergoes a very fast disproportionation reaction leading to the loss of the catalyst via the production of inactive solid cobalt [12]. Although this drawback is not encountered with vitamin B12 or ligands such as bipyridine and salen [13][14][15][16][17][18][19][20][21][22][23][24][25][26], the cobalt(I) species, obtained under these conditions, are too stable to efficiently react with aromatic halides, ArX. The use of pyridine as co-solvent was finally found to be a good compromise except for coupling reactions involving electrophiles.…”

Section: Introductionmentioning

confidence: 99%