Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-6134
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 |
Year of first publication: | 2020 |
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 |
ROR: | https://ror.org/023b0x485 |
DOI: | http://doi.org/10.25358/openscience-6134 |
Version: | Published version |
Publication type: | Zeitschriftenaufsatz |
License: | CC BY-NC-ND |
Information on rights of use: | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
Journal: | Chemistry - a European journal 26 72 |
Pages or article number: | 17574 17580 |
Publisher: | Wiley-VCH |
Publisher place: | Weinheim |
Issue date: | 2020 |
ISSN: | 15213765 |
Publisher URL: | https://doi.org/10.1002/chem.202003852 |
Publisher DOI: | 10.1002/chem.202003852 |
Appears in collections: | JGU-Publikationen |
Files in This Item:
File | Description | Size | Format | ||
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wesenberg_lars_j.-metal-free_two-20210628202809000.pdf | 1.45 MB | Adobe PDF | View/Open |