两个光子胜过一个光子：通过双重光化学激活的 Paternò-Büchi 反应连续流合成ꞵ-内酯

IF 2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Flow Chemistry Pub Date : 2023-12-15 DOI:10.1007/s41981-023-00297-7

Federica Minuto, Emanuele Farinini, Serena De Negri, Riccardo Leardi, Davide Ravelli, Pavlo Solokha, Andrea Basso

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引用次数: 0

摘要

在本文中，我们报告了烯酮与苯并吡啶之间的[2 + 2]环加成反应，该反应的特点是由可见光引发的不寻常的双重光化学活化。采用流动系统并通过 "实验设计 "对反应条件进行优化后，相应的 β-内酯的产率达到了中等到良好的水平。通过全面的计算分析，阐明了反应机理，并证明了观察到的非对映选择性。该反应还成功地用混合苯进行了测试，显示出完全的区域选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Two photons are better than one: continuous flow synthesis of ꞵ-lactones through a doubly photochemically-activated Paternò-Büchi reaction

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Two photons are better than one: continuous flow synthesis of ꞵ-lactones through a doubly photochemically-activated Paternò-Büchi reaction

In this paper we report a [2 + 2] cycloaddition reaction between ketenes and benzils, characterized by an unusual double photochemical activation triggered by visible light. Employment of a flow system and optimization of reaction conditions through Design of Experiments resulted in moderate to good yields of the corresponding β-lactones. A thorough computational analysis allowed to elucidate the mechanism of the reaction and justify the observed diastereoselectivity. The reaction was also successfully tested with mixed benzils, showing complete regioselectivity.

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来源期刊

Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

6.40

自引率

3.70%

发文量

审稿时长

>12 weeks

期刊介绍： The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.