6533b870fe1ef96bd12d05d2

RESEARCH PRODUCT

Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives.

Bernd ElslerSiegfried R. WaldvogelRobert FrankeLara SchulzDieter SchollmeyerKatrin Marie DyballaEnders Mathias

subject

010405 organic chemistryInorganic chemistryGeneral ChemistryGlassy carbon010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesAnodechemistry.chemical_compoundAnilinechemistryMetal freeReagentPolymer chemistryCoupling (piping)Amine gas treating

description

The dehydrogenative cross-coupling of aniline derivatives to 2,2′-diaminobiaryls is reported. The oxidation is carried out electrochemically, which avoids the use of metals and reagents. A large variety of biphenyldiamines were thus prepared. The best results were obtained when glassy carbon was used as the anode material. The electrosynthetic reaction is easily performed in an undivided cell at slightly elevated temperature. In addition, common amine protecting groups based on carboxylic acids were employed that can be selectively removed under mild conditions after the cross-coupling, which provides quick and efficient access to important building blocks featuring free amine moieties.

10.1002/anie.201612613https://pubmed.ncbi.nlm.nih.gov/28252240