Review on the electrochemistry of solvated electrons. Its use in hydrogenation of monobenzenoids

Andel‐Scheffer, P. J. M. van; Barendrecht, E Embrecht

doi:10.1002/recl.19951140602

Cited by 9 publications

(6 citation statements)

References 98 publications

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“…The most practical method for large‐scale reactions is a solution of alkali metals in liquid ammonia [6] . However, electrochemical [7] or very recent photocatalytic reductions [8] have been developed as well.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Krüger

Linker

2021

Eur J Org Chem

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A convenient method for the synthesis of γ‐spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl‐substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new γ‐spirolactams have been synthesized in analytically pure form.

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Section: Introductionmentioning

confidence: 99%

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Krüger

Linker

2021

Eur J Org Chem

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“…ECH of simple aromatic compounds, polyaromatic compounds and phenols have been studied earlier for optimizing reaction conditions [209,213–215] . A report on ECH of phenols on Pt/C and Pd/C, compared the observations with previous results obtained for phenol conversion on Rh/C [50] .…”

Section: Electrochemical Hydrogenation Reactions (Ech)mentioning

confidence: 99%

“…Didodecyldimethylammonium bromide (DDAB) was the surfactant used for the experiment. The use of cationic surfactants strongly enhanced the extent and efficiency of ECH of unsaturated compounds by incorporation of the organic substrate in a hydrophobic surfactant layer adsorbed on the cathode [209,229] . The association of organic substrates with micelles and surfactant layers depended on their hydrophobicity, which increased with the number and length of alkyl substituents.…”

Section: Electrochemical Hydrogenation Reactions (Ech)mentioning

confidence: 99%

“…[208] S. N. Chaudhuri et al reported the use of nickel on various oxides like aluminium oxideα-Al 2 O 3 , γ-Al 2 O 3 , silicon dioxide (SiO 2 ) (as Kieselguhr) and magnesium oxide (MgO) for catalytic hydrogenation of benzene. [81] Similarly, several chemists worked on conventional hydrogenation of benzene, especially in the early 1900s, [209][210][211][212] all involving the use of transitional metal catalysts, high temperatures and high pressures.…”

Section: Electrochemical Hydrogenation Of Aromatic Carbocyclesmentioning

confidence: 99%

“…Early researchers have worked on ECH of simple aromatic compounds, polyaromatic compounds and phenols in several reports, trying to set the method for optimum results. [209,[213][214][215][216] Since the use of such high temperatures and pressure is not economical, safe, and green, electrochemical methods are being continually optimised for their reduction at ambient conditions.…”

Section: Electrochemical Hydrogenation Of Aromatic Carbocyclesmentioning

confidence: 99%

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Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Jayan,

Thadathil,

Varghese

2023

Asian J Org Chem

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Conventional methods for hydrogenation of organic compounds generally use corrosive catalysts and reagents, along with extreme conditions like high temperatures and pressures. Quenching of corrosive materials does not deter its negative impact on the environment, nor is one safe when it comes to working with high temperature and pressure. Electrochemical hydrogenation has proven to be safe and green since most of the efficient reactions are conducted at ambient pressure and temperature, without or minimizing the use of toxic catalysts and corrosive reagents as compared to conventional methods. This review therefore presents the advances in electrochemical hydrogenation reactions of organic compounds, starting from simple aliphatic compounds to complex polyaromatics and heterocyclic aromatic compounds.

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Advances in Electrochemical Hydrogenation Since 2010

et al. 2021

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A commitment to developing a convenient, efficient, and safe hydrogenation strategy is one of the main focuses of industry and academia. Electrochemical hydrogenation brings greener and gentler opportunities for the selective hydrogenation of unsaturated compounds and the incorporation of deuterium atoms to desired products with traceless electrons as redox reagents in the absence of highpressure hydrogen. In this account, recent advances in electrochemical hydrogenation or transfer hydrogenation of unsaturated compounds since 2010 are summarized. The reaction features, limitations, substrates scopes, mechanism of these hydrogenation reactions are discussed in this review. We hope this account will contribute to future developments to broaden the scope of electrochemical hydrogenation or transfer hydrogenation. Alkenes and Alkynes 2.3. Electrochemical Hydrogenation of Unactivated Alkenes and Alkynes 2.4. Electrochemical Hydrogenation of N-Heteroaromatics 2.5. Electrochemical Birch Reduction 3. Conclusion

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Review on the electrochemistry of solvated electrons. Its use in hydrogenation of monobenzenoids

Cited by 9 publications

References 98 publications

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Synthesis of γ‐Spirolactams by Birch Reduction of Arenes

Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Advances in Electrochemical Hydrogenation Since 2010

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