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Gold-catalyzed oxidative hydroacylation reactions of α-iminoalkynes with aldehydes and O2

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Abstract

Gold-catalyzed aerobic oxidations of α-iminoalkynes with aryl aldehydes led to oxidative 1,3-hydroacyclation reactions, yielding high Z-selectivity. We performed 2H- and 18O-labeling experiments to confirm the role of water as an oxygen donor and O2 as the main oxidant. The Z-selectivity arises from an efficient conjugation between the enone and its aryl substituent. We postulate an initial [4+2]-annulation of α-iminoalkynes with aldehydes to form a six-membered oxonium species that is attacked by water, followed by the O2 oxidation of a key intermediate.

Graphical abstract: Gold-catalyzed oxidative hydroacylation reactions of α-iminoalkynes with aldehydes and O2

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Publication details

The article was received on 03 May 2017, accepted on 08 May 2017 and first published on 12 May 2017


Article type: Communication
DOI: 10.1039/C7CC03421K
Citation: Chem. Commun., 2017, Advance Article
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    Gold-catalyzed oxidative hydroacylation reactions of α-iminoalkynes with aldehydes and O2

    Y. Hsu, J. Lai and R. Liu, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC03421K

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