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Issue 10, 2019
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Dinuclear manganese alkoxide complexes as catalysts for C–N bond cleavage of simple tertiary N,N-dialkylamides to give esters

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Abstract

Amide bonds are stable due to the resonance between the nitrogen lone pair and the carbonyl moiety, and therefore the chemical transformation of amides, especially tertiary amides, involving C–N bond fission is considered one of the most difficult organic reactions, unavoidably requiring harsh reaction conditions and strong acids or bases. We report the catalytic C–N bond cleavage of simple tertiary N,N-dialkylamides to give corresponding esters using a catalyst system (2 mol% based on Mn atoms) of a tetranuclear manganese alkoxide, [Mn(acac)(OEt)(EtOH)]4 (1c), combined with four equivalents of 4,7-bis(dimethylamino)-1,10-phenanthroline (L1: Me2N-Phen). Regarding the reaction mechanism, we isolated a dinuclear manganese complex, [Mn(acac)(OEt)(Phen)]2 (6c), which was revealed as the catalytically active species for the esterification of tertiary amides.

Graphical abstract: Dinuclear manganese alkoxide complexes as catalysts for C–N bond cleavage of simple tertiary N,N-dialkylamides to give esters

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Publication details

The article was received on 31 Dec 2018, accepted on 28 Jan 2019 and first published on 29 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05819A
Chem. Sci., 2019,10, 2860-2868
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Dinuclear manganese alkoxide complexes as catalysts for C–N bond cleavage of simple tertiary N,N-dialkylamides to give esters

    H. Nagae, T. Hirai, D. Kato, S. Soma, S. Akebi and K. Mashima, Chem. Sci., 2019, 10, 2860
    DOI: 10.1039/C8SC05819A

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