无金属催化烯烃自由基环化合成多氟取代吲哚酮

doi:10.11944/j.issn.1000-0518.2015.11.150108

摘要/Abstract

摘要：

一种无金属催化的活泼烯烃与全氟碘代丁烷自由基环化合成含氟吲哚酮的反应被发展。在廉价易得的的偶氮二异丁腈(AIBN)介导下, 多种N-芳基丙烯酰胺类化合物与全氟碘代丁烷发生自由基串联环化反应,以53%~85%的产率合成了一系列的潜在生理活性的多氟取代吲哚酮。此工作为潜在药用价值的多氟取代吲哚酮合成提供了一条高效、廉价、绿色的新途径。

关键词: 无金属催化, 偶氮二异丁腈, C—H环化, 自由基, 多氟吲哚酮

Abstract:

A metal-free cyclization reaction of activated alkenes with nonafluorobutyl iodide toward perfluorinated oxindoles was developed. In the presence of azodiisobutyronitrile(AIBN), various N-arylacrylamide underwent radical cyclization smoothly to afford a series of synthetically important perfluorinated oxindoles in 53%~85% yields. This work provides a novel high efficient, cheap and green route for the synthesis of perfluorinated oxindoles having potential medicinal values.

Key words: metal-free, azodiisobutyronitrile, C—H cyclization, radical, perfluorinated oxindole

唐石, 邓佑林, 王琼, 甘亚兵, 袁世亮, 李志豪, 邹湘祁. 无金属催化烯烃自由基环化合成多氟取代吲哚酮[J]. 应用化学, 2015, 32(11): 1246-1252.

TANG Shi, LI Zhihao, DENG Youlin, GAN Yabing, YUAN Shiliang, ZHOU Xiangqi. Metal-free Cyclization of Alkenes Toward Perfluorinated Oxindoles[J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1246-1252.

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