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可见光诱导连续二氟甲基化去芳构化、羟化和氧化合成Gem-二氟螺-γ-内酰胺氧吲哚

Synthesis of gem-Difluorinated Spiro-γ-lactam Oxindoles by Visible-Light-Induced Consecutive Difluoromethylative Dearomatization, Hydroxylation, and Oxidation.

机构信息

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of, Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, P. R. China.

出版信息

Chemistry. 2018 Aug 6;24(44):11283-11287. doi: 10.1002/chem.201802141. Epub 2018 Jul 9.

Abstract

Described herein is a protocol for visible-light-induced consecutive synthesis of gem-difluorinated spiro-γ-lactam oxindoles under mild conditions by means of a process involving sequential radical difluoromethylative dearomatization, hydroxylation, and oxidation. The protocol features high chemo- and regioselectivity, good functional group tolerance, and easy scalability. Several of the functionalized spirooxindole products showed good fungicidal activity, suggesting that they have potential agrochemical applications.

摘要

本文描述了一种在温和条件下通过可见光诱导的连续合成方法,实现了 gem-二氟化螺-γ-内酰胺氧吲哚的串联合成。该过程涉及顺序自由基二氟甲基化去芳构化、羟化和氧化反应。该方法具有高的化学和区域选择性、良好的官能团耐受性和易于扩大规模的特点。一些功能化的螺氧吲哚产物表现出良好的杀菌活性,表明它们具有潜在的农用化学品应用前景。

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