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

Yu-Chen Hsu, Jing-He LaiRai-Shung Liu
Chemical Communications, 卷.53(44), 頁碼.6009-6012
2017

摘要

Catalysis Electronic Optical and Magnetic Materials Ceramics and Composites Chemistry (all) Surfaces Coatings and Films Metals and Alloys Materials Chemistry
Gold-catalyzed aerobic oxidations of α-iminoalkynes with aryl aldehydes led to oxidative 1,3-hydroacyclation reactions, yielding high Z-selectivity. We performed 2 H- and 18 O-labeling experiments to confirm the role of water as an oxygen donor and O 2 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 O 2 oxidation of a key intermediate.

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