Elektroreduktion organischer Verbindungen. 22. Darstellung aromatischer Aldehyde durch Elektroreduktion von Estern und Amiden in Gegenwart von Chlortrimethylsilan

Goetz‐Schatowitz, P.‐R.; Struth, G.; Voß, Jürgen; Wiegand, G.

doi:10.1002/prac.19933350304

Cited by 11 publications

(5 citation statements)

References 31 publications

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“…Alkylbenzoate esters and amides, for example, have been cleanly reduced to the corresponding aldehydes with the help of chlorotrimethylsilane in up to 64% yields [84]. Acyl halides and aliphatic amides have also been converted to aldehydes, albeit in modest yields [85].…”

Section: Electrochemicalmentioning

confidence: 99%

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Luca

Fenwick

2015

Journal of Photochemistry and Photobiology B: Biology

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Available online xxxx a b s t r a c tThe present review covers organic transformations involved in the reduction of CO 2 to chemical fuels. In particular, we focus on reactions of CO 2 with organic molecules to yield carboxylic acid derivatives as a first step in CO 2 reduction reaction sequences. These biomimetic initial steps create opportunities for tandem electrochemical/chemical reductions. We draw parallels between long-standing knowledge of CO 2 reactivity from organic chemistry, organocatalysis, surface science and electrocatalysis. We point out some possible non-faradaic chemical reactions that may contribute to product distributions in the production of solar fuels from CO 2 . These reactions may be accelerated by thermal effects such as resistive heating and illumination.

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Section: Electrochemicalmentioning

confidence: 99%

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Luca

Fenwick

2015

Journal of Photochemistry and Photobiology B: Biology

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“…In this context, electrochemical deoxygenation represents an attractive alternative to conventional methods. [13] Owing to the high reduction potentials of carboxamides, either these species have to be activated by strong acids in high concentration or the oxygen species has to be trapped by sacrificial anodes [14] or silylation agents [15] to achieve conversion. Some studies report on the electrochemical reduction of amides to amines with the coformation of water.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Deoxygenation of Aromatic Amides and Sulfoxides

Edinger

Waldvogel

2014

Eur J Org Chem

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The electrochemical deoxygenation of a broad range of aromatic amides was achieved under mild conditions on lead cathodes. Under the optimized reaction conditions, acetal, thienyl, and ether moieties are tolerated. Furthermore, the reduction protocol can be applied to aromatic and aliphatic sulfoxides to obtain the corresponding sulfides. For both aromatic amides and sulfoxides, the deoxygenation reaction ensues without the use of expensive catalysts or hazardous reducing agents. Owing to the high selectivity of the process, simple extraction is sufficient to isolate the product from the substrate. The straightforward purification protocol, the coformation of water, and the use of electric current instead of reducing agents render our method environmentally friendly and economically beneficial.

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“…It is thought that H + ion reduction at the cathode was largely suppressed by the pres-ence of n Bu 4 N + ions, which got adsorbed onto the cathode surface. 89 Electrosynthetic methods for the cathodic reduction of amides to produce aldehydes 90 and alcohols 91 also exist.…”

Section: Precursors To Other Functional Groupsmentioning

confidence: 99%