Electrogenerated acid

An endo-selective ionic Diels-Alder reaction of a,/f-enone and a,/f-enal acetals catalyzed by electrogenerated acid [99]... 

Heptyl 3-Phenylpropyl Ether [Electrogenerated Acid-Promoted Reduction of an Aldehyde to an Unsymmetrical Ether].333 A mixture of 1-heptanal (1.0 mmol), 3-phenylpropoxytrimethylsilane (1.2 mmol), tetra-n-butylammonium perchlorate (0.1 mmol), and lithium perchlorate (0.1 mmol) was dissolved in CH2CI2 (3 mL) in an undivided cell. The mixture was electrolyzed under constant current (1.67 mA cm-2) with platinum electrodes at ambient temperature. After 5 minutes, dimethylphenylsilane (1.2 mmol) was added drop-wise and the electrolysis was continued (0.06 Faraday/mol). After completion of the reaction, one drop of Et3N was added and the solution was concentrated. The residue was chromatographed on Si02 to give 1-heptyl 3-phenylpropyl... 

Electrogenerated acid (EG acid), aldehyde to alcohol reduction, etherification, 65-69... 

The thus prepared /l-trifluoromethylated 0,S-acetal 4 allows us to make a carbon-carbon bond via a carbocation at the -position to the CF 3 group as shown in Scheme 6.9 [48]. Interestingly, Lewis acid-mediated allylation and cyanation can be achieved efficiently only when electrogenerated acids (EGA) are employed. 

Electrogenerated acids (EGAs) are strong Bronsted acids arising from protons produced directly or indirectly in an anodic... 

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