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Reagent‐ and Metal‐Free Anodic C−C Cross‐Coupling of Aniline Derivatives
Author(s) -
Schulz Lara,
Enders Mathias,
Elsler Bernd,
Schollmeyer Dieter,
Dyballa Katrin M.,
Franke Robert,
Waldvogel Siegfried R.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201612613
Subject(s) - aniline , reagent , amine gas treating , anode , chemistry , coupling reaction , combinatorial chemistry , metal , polymer chemistry , organic chemistry , electrode , catalysis
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.