N-Substituted 1-Aminoindoles from Electrogenerated N-Substituted 2-(ortho-Nitrosophenyl)ethylamines

Cathodic Corrosion of Metal Electrodes—How to Prevent It in Electroorganic Synthesis

“…The research group of Moinet pioneered the technique and used it in the generation of nitrosobenzene derivatives from nitroarenes through hydroxylamines in several studies. 238 − 246 After that, only a few examples of electrosyntheses have been published, wherein both electrodes are required for the same process. 1 , 247 , 248 Hartmer and Waldvogel developed a domino oxidation–reduction sequence for the conversion of aldoximes to nitriles, where the first redox process is carried out on graphite anode and lead cathode is used in the second to generate the final compounds ( Scheme 18 ).…”

Toward Acetylene Renaissance: Functionally Rich N-Aminoindoles from Acetylene Gas, Ketones, and Hydrazines in Two Steps

“…16 In addition, N-aminoindoles were synthesized electrochemically from 2-(o-nitrosophenyl)ethylamines. 17 Recently, several reports have appeared on the Rh-catalyzed syntheses of N-aminoindoles by the cyclization of acylhydrazines with diazo compounds 18 or alkynes, 19 arylsubstituted diazenecarboxylates with alkenes, 20 and threecomponent annulation of arylhydrazines, diazo compounds, and ketones. 21 Eventually, the development of direct and efficient synthetic strategies to build N-aminoindoles, particularly highly functionalized ones, based on the principles of the pot-atomstep-economy (PASE) paradigm 22 from available and inexpensive precursors under transition metal-free conditions, is strongly desired.…”