Access to cyclobutane–fused dihydrobenzothiophenes via gold–mediated photocatalyzed [2+2]–cycloaddition reactions

IF 6.5 1区化学 Q2 CHEMISTRY, PHYSICAL Journal of Catalysis Pub Date : 2024-11-21 DOI:10.1016/j.jcat.2024.115850

Ekaterina A. Martynova, Vladislav V. Voloshkin, Marco Villa, Antonio Fiorentino, Marek Beliš, Kristof Van Hecke, Paola Ceroni, Steven P. Nolan

引用次数: 0

Abstract

The use of [Au(SIPr)(Cbz)] as photosensitizer in [2+2]–cycloaddition reactions between benzothiophenes and activated (and non–activated) alkenes is presented. Commonly used organic and Ir–photosensitizers proved inefficient in the reaction with non–activated alkenes. The study emphasizes the dependence of the nature of the alkene, a parameter that has previously received little attention. Under mild reaction conditions, a wide array of alkenes and benzothiophenes were successfully coupled, showcasing remarkable tolerance of diverse functional groups. Additionally, we present intramolecular [2+2]–cycloaddition reactions, including benzothiophenes featuring various alkene linkers at the C2 and C3 positions.

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通过金介导的光催化[2+2]-环加成反应获得环丁烷融合二氢苯并噻吩

介绍了在苯并噻吩与活化（和非活化）烯烃的 [2+2]- 碳加成反应中使用 [Au(SIPr)(Cbz)] 作为光敏剂的情况。事实证明，常用的有机光敏剂和离子光敏剂在与非活化烯的反应中效率低下。研究强调了烯烃性质的依赖性，而这一参数以前很少受到关注。在温和的反应条件下，一系列烯烃和苯并噻吩被成功偶联，显示了对不同官能团的显著耐受性。此外，我们还介绍了分子内 [2+2]-cycloaddition 反应，包括在 C2 和 C3 位置具有各种烯连接物的苯并噻吩。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Catalysis 工程技术-工程：化工

CiteScore

12.30

自引率

5.50%

发文量

447

审稿时长

31 days

期刊介绍： The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes. The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods. The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.