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通过锌催化的N-磺酰基烯酰胺分子间氧化合成α,β-不饱和N-磺酰基亚胺

Synthesis of α,β-Unsaturated N-Sulfonyl Imides through Zinc-Catalyzed Intermolecular Oxidation of N-Sulfonyl Ynamides.

作者信息

Pan Fei, Shu Chao, Ping Yi-Fan, Pan Yi-Fei, Ruan Peng-Peng, Fei Qian-Ran, Ye Long-Wu

机构信息

State Key Laboratory of Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University , Xiamen 361005, P. R. China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, P. R. China.

出版信息

J Org Chem. 2015 Oct 16;80(20):10009-15. doi: 10.1021/acs.joc.5b01608. Epub 2015 Oct 8.

Abstract

A novel zinc-catalyzed intermolecular oxidation of N-sulfonyl ynamides has been developed. A variety of functionalized α,β-unsaturated N-sulfonyl imides are readily accessed by utilizing this approach, thus providing a viable alternative to synthetically useful α,β-unsaturated imides. Importantly, the reaction is proposed to proceed by a vinyligous E2-type elimination pathway, but not metal carbene pathway.

摘要

已开发出一种新型锌催化的N-磺酰基烯炔酰胺的分子间氧化反应。利用这种方法可以很容易地获得各种功能化的α,β-不饱和N-磺酰基亚胺,从而为合成有用的α,β-不饱和亚胺提供了一种可行的替代方法。重要的是,该反应被认为是通过类似乙烯基E2型消除途径进行的,而不是金属卡宾途径。

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