Twofold Electrochemical Amination of Naphthalene and Related Arenes. Issue 9 (22nd June 2017)

• Record Type: Journal Article
• Authors: Möhle, Sabine; Herold, Sebastian; Richter, Frank; Nefzger, Hartmut; Waldvogel, Siegfried R.
• Is Part Of: ChemElectroChem. Volume 4:Issue 9(2017)
• Page Start: 2196
• Page End: 2210
• Publication Date: 2017-06-22
• Subjects: BDD anode -- oxidation -- sustainable synthesis -- pyridinium salts -- electrochemical synthesis; Electrochemistry -- Periodicals; 541.37
• DOI: 10.1002/celc.201700476
• Languages: English
• ISSNs: 2196-0216

Abstract

Abstract: The twofold electrochemical amination reaction of polycyclic arenes, such as naphthalene (4 ), via Zincke intermediates is demonstrated for the first time. The installation of nitrogen functionalities occurs regioselectively in positions 1 and 5 of naphthalene (4 ). The key for this electroconversion is boron‐doped diamond as the anode material. The method of the multi‐amination reaction is expanded to other aromatic substrates. A detailed study is provided, covering electrolysis parameters such as anode material, electrolyte system, current density, separator, and so forth. Despite the moderate yields, this approach offers the first direct electrosynthetic access to diaminated products. Abstract : Diamonds are forever : Twofold aminated with the power of diamond anodes are naphthalene and related arenes. This electro‐organic synthesis provides the first and highly regioselective access to 1, 5‐diaminonaphthalene. Larger polycyclic aromatic compounds, conformationally flexible, or non‐conjugated substrates yield several diaminated isomers.