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Issue 88, 2016
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Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene

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Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita–Baylis–Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.

Graphical abstract: Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene

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Publication details

The article was received on 27 Jul 2016, accepted on 30 Sep 2016 and first published on 17 Oct 2016

Article type: Communication
DOI: 10.1039/C6CC06201F
Citation: Chem. Commun., 2016,52, 12980-12983
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    Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene

    X. Lu and U. Schneider, Chem. Commun., 2016, 52, 12980
    DOI: 10.1039/C6CC06201F

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