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光驱动的四组分反应:硼酸盐衍生物作为烷基化试剂:一种通过胺/亚胺介导的激活方法。

Light-Driven Four-Component Reaction with Boronic Acid Derivatives as Alkylating Agents: An Amine/Imine-Mediated Activation Approach.

机构信息

Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.

Department of General and Inorganic Chemistry, Faculty of Chemistry, University of Havana, Zapata y G, Havana 10400, Cuba.

出版信息

Org Lett. 2023 Jun 9;25(22):4010-4015. doi: 10.1021/acs.orglett.3c01020. Epub 2023 May 30.

Abstract

Herein, we describe a one-pot aminoalkylation of styrene derivatives with boronic acids (BAs) and boronic acid pinacol esters as radical precursors for the synthesis of complex secondary amines in moderate to high yields through a mild and easily accessible organophotoredox-catalytic four-component reaction. Additionally, we report for the first time in a photoredox process the activation of alkyl boronic acid derivatives by imines, which play a dual role in the reaction as both substrate and Lewis base activator. The protocol applicability was greatly enhanced by its successful adaptation to photoflow reactors.

摘要

在这里,我们描述了一种将苯乙烯衍生物与硼酸(BAs)和硼酸频哪醇酯一锅法进行氨基烷基化的方法,这些硼酸和硼酸频哪醇酯作为自由基前体,通过温和且易于获得的有机光氧化还原催化的四组分反应,以中等至高产率合成复杂的仲胺。此外,我们首次在光氧化还原过程中报道了亚胺对烷基硼酸衍生物的活化,亚胺在反应中起双重作用,既是底物又是路易斯碱活化剂。通过成功地将其适应于光流反应器,大大提高了该方案的适用性。

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