Electrochemical Dehydrogenative C(sp2 )-H Amination

Mahesh Puthanveedu; Vladislav Khamraev; Lukas Brieger; Carsten Strohmann; Andrey P Antonchick

doi:10.1002/chem.202100960

Electrochemical Dehydrogenative C(sp² )-H Amination

Chemistry. 2021 May 26;27(30):8008-8012. doi: 10.1002/chem.202100960. Epub 2021 May 1.

Authors

Mahesh Puthanveedu^{1

2}, Vladislav Khamraev^{2

3

4}, Lukas Brieger⁵, Carsten Strohmann⁵, Andrey P Antonchick^{1

2

6}

Affiliations

¹ Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227, Dortmund, Germany.
² Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Chemische Biologie, Otto-Hahn-Straße 4a, 44221, Dortmund, Germany.
³ North Caucasus Federal University, Department of Chemistry, 1a Pushkin St., 355009, Stavropol, Russian Federation.
⁴ Present address: D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, 125047, Moscow, Russian Federation.
⁵ Technische Universität Dortmund, Fakultät für Chemie und Chemische Biologie, Anorganische Chemie, Otto-Hahn-Straße 6, 44227, Dortmund, Germany.
⁶ Nottingham Trent University, College of Science and Technology, Department of Chemistry and Forensics, Clifton Lane, NG11 8NS, Nottingham, UK.

Abstract

A transition-metal-free direct electrolytic C-H amination involving an electrochemically generated nitrenium ion intermediate has been developed. The electrosynthesis takes place in the absence of any organoiodine catalysts and is enabled by an in situ generated electrolyte. A novel, efficient intramolecular and intermolecular C-H amination has been demonstrated using a simple reaction setup.

Keywords: amination; carbazole; electrochemistry; heterocycles; nitrenium ion.

Abstract

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