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Authors: Wesenberg, Lars J.
Diehl, Erika
Zähringer, Till J. B.
Dörr, Carolin
Schollmeyer, Dieter
Shimizu, Akihiro
Yoshida, Jun-ichi
Hellmich, Ute A.
Waldvogel, Siegfried R.
Title: Metal-free twofold electrochemical C−H amination of activated arenes : application to medicinally relevant precursor synthesis
Online publication date: 29-Jun-2021
Language: english
Abstract: The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non-protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C−N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against castrate-resistant prostate cancer. Further improvement of the structure led to significantly increased cancer cell line toxicity. Thus, exploiting environmentally benign electrooxidation, we present a new versatile and powerful method based on direct C−H activation that is applicable for example the production of medicinally relevant compounds.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
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Journal: Chemistry - a European journal
Pages or article number: 17574
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2020
ISSN: 15213765
Publisher URL:
Publisher DOI: 10.1002/chem.202003852
Appears in collections:JGU-Publikationen

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