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Chromium-Catalyzed Alkylation of Amines by Alcohols

DOI zum Zitieren der Version auf EPub Bayreuth: https://doi.org/10.15495/EPub_UBT_00005028
URN to cite this document: urn:nbn:de:bvb:703-epub-5028-3

Title data

Kallmeier, Fabian ; Fertig, Robin ; Irrgang, Torsten ; Kempe, Rhett:
Chromium-Catalyzed Alkylation of Amines by Alcohols.
In: Angewandte Chemie International Edition. Vol. 59 (2020) Issue 29 . - pp. 11789-11793.
ISSN 1521-3773
DOI der Verlagsversion: https://doi.org/10.1002/anie.202001704

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Project information

Project financing: Deutsche Forschungsgemeinschaft

Abstract

The alkylation of amines by alcohols is a broadly applicable, sustainable, and selective method for the synthesis of alkyl amines, which are important bulk and fine chemicals, pharmaceuticals, or agrochemicals. Here we report that Cr complexes can catalyze this C‐N bond formation reaction. We synthesized and isolated 35 examples of alkylated amines. Thirteen previously undisclosed products could be obtained and the use of amino alcohols as alkylating agents could be demonstrated. The catalyst tolerates numerous functional groups, among them hydrogenation sensitive examples. In comparison to many other alcohol‐based amine alkylation protocols where a stoichiometric amount of base is required, our Cr based catalyst system permits product isolation with yields higher than 90% for various alkyl amines with a catalytic amount of base only. Our study indicates that Cr complexes can catalyze borrowing hydrogen or hydrogen auto‐transfer reactions and, thus, could be an alternative to Fe, Co and Mn or noble metals in (de)hydrogenation catalysis.

Further data

Item Type: Article in a journal
Keywords: alcohols, alkylation, borrowing-hydrogen reactions, chromium, hydrogen autotransfer
DDC Subjects: 500 Science > 540 Chemistry
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Inorganic Chemistry II > Chair Inorganic Chemistry II - Univ.-Prof. Dr. Rhett Kempe
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Inorganic Chemistry II
Language: English
Originates at UBT: Yes
URN: urn:nbn:de:bvb:703-epub-5028-3
Date Deposited: 11 Sep 2020 05:41
Last Modified: 11 Sep 2020 05:41
URI: https://epub.uni-bayreuth.de/id/eprint/5028

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