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

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Gold-catalyzed oxidative hydroacylation reactions of α-iminoalkynes with aldehydes and O2
Chemical Communications ( IF 4.3 ) Pub Date : 2017-05-12 00:00:00 , DOI: 10.1039/c7cc03421k
Yu-Chen Hsu _{1,

2,

3,

4} , Jing-He Lai _{1,

2,

3,

4} , Rai-Shung Liu _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

金催化的α-亚氨基炔烃与醛和O _2的氧化加氢酰化反应

金催化的α-亚氨基炔烃与芳基醛的需氧氧化导致氧化的1,3-氢环化反应，产生高Z选择性。我们进行了^2次H-标记和^18次O-标记实验，以确认水作为氧气供体和O ₂作为主要氧化剂的作用。所述ž -选择性起因于烯酮和其芳基取代基之间的有效偶联。我们假设α-亚氨基炔烃与醛的初始[4 + 2]环化反应形成六元的氧鎓类物质，该类物质受到水的攻击，然后被关键中间体的O ₂氧化。

更新日期：2017-05-19

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