n -甲基- n -取代-[1,1 ' -联芳基]-2-胺在可见光诱导下的无金属和无光催化剂氧化分子内环化：易于获得非苯三啶酮

IF 4.7 3区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Photochemistry and Photobiology A-chemistry Pub Date : 2025-09-29 DOI:10.1016/j.jphotochem.2025.116812

Palani Natarajan, Partigya, Pooja, Priya, Meena

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引用次数: 0

摘要

建立了以n -甲基- n -取代-[1,1 ' -联芳基]-2胺、分子氧（气球）、n -碘琥珀酰亚胺（NIS）和DCE为原料，在可见光诱导下合成一系列吩并吡啶酮的方法。该方法不需要光敏剂或任何金属试剂，因为n -甲基- n -取代-[1,1 ' -联芳基]-2-胺和NIS形成电子供体-受体络合物，允许在可见光照射下以较高的收率生产所需的菲苯二酮。此外，与文献报道的n -取代-[1,1 ' -联芳基]-2胺合成菲苯二酮的方法相比，该方法温和，易于使用，不含金属，无毒co，并且在室温下工作。在可见光作用下，首次将n -甲基- n -取代-[1,1′-联芳基]-2-胺转化为菲苯二酮。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Visible-light-induced metal- and photocatalyst-free oxidative intramolecular cyclization of N-methyl-N-substituted-[1,1′-biaryl]-2-amines: facile access to phenanthridinones

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Visible-light-induced metal- and photocatalyst-free oxidative intramolecular cyclization of N-methyl-N-substituted-[1,1′-biaryl]-2-amines: facile access to phenanthridinones

A visible-light-induced strategy for the synthesis of a series of phenanthridinones from readily accessible N-methyl-N-substituted-[1,1′-biaryl]-2-amines, molecular oxygen (balloon), N-iodosuccinimide (NIS) and DCE has been established. This method does not require a photosensitizer or any metal reagent because N-methyl-N-substituted-[1,1′-biaryl]-2-amines and NIS form an electron donor-acceptor complex that allows the production of desired phenanthridinones in good yields under visible-light irradiation. Moreover, in contrast to literature reported methods of synthesis of phenanthridinones from N-substituted-[1,1′-biaryl]-2-amines, this procedure is mild, easy to use, metal-free, toxic CO-free, and works at room temperature. Furthermore, under the action of visible-light, this is the first method to convert N-methyl-N-substituted-[1,1′-biaryl]-2-amines into phenanthridinones.

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来源期刊

Journal of Photochemistry and Photobiology A-chemistry 化学-物理化学

CiteScore

7.90

自引率

7.00%

发文量

580

审稿时长

48 days

期刊介绍： JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds. All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor). The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.