Dinuclear manganese alkoxide complexes as catalysts for C-N bond cleavage of simple tertiary N,N-dialkylamides to give esters.
Chem Sci
; 10(10): 2860-2868, 2019 Mar 14.
Article
em En
| MEDLINE
| ID: mdl-30996863
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.
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Base de dados:
MEDLINE
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En
Ano de publicação:
2019
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Article