4.5 Article

Metal- and Reagent-Free Anodic Dehydrogenative Cross-Coupling of Naphthylamines with Phenols

Journal

CHEMELECTROCHEM
Volume 5, Issue 9, Pages 1249-1252

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/celc.201800050

Keywords

N,O ligands; cross-coupling; dehydrogenation; electrochemistry; anode

Funding

  1. DFG [Wa1276/14-1]
  2. Advanced Lab of Electrochemistry and Electrosynthesis - ELYSION (Carl Zeiss Stiftung)
  3. Center for INnovative and Emerging MAterials (CINEMA)

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The first electrochemical dehydrogenative anodic cross-coupling of naphthylamines with phenols was established to access a broad variety of non-symmetrical, hetero-bidentate N,O-biaryl motifs. By anodic oxidation, we provide a sustainable and inherently safe method, which avoids the need for pre-functionalization of the starting materials. Hence, the elaborated electrochemical protocol simplifies the synthesis of the desired C-1-symmetrical biaryls drastically. Furthermore, the use of electricity as a reagent contributes to the idea of green chemistry as metal catalysts and stoichiometric oxidizers are omitted.

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