Visible-Light-Induced Oxazoline Formations from N-Vinyl Amides Catalyzed by an Ion-Pair Charge-Transfer Complex,ACS Catalysis

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Visible-Light-Induced Oxazoline Formations from N-Vinyl Amides Catalyzed by an Ion-Pair Charge-Transfer Complex
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-09-08 , DOI: 10.1021/acscatal.1c01755
Rui Sun ₁ , Xiao Yang ₁ , Yicen Ge ₂ , Jintong Song ₁ , Xueli Zheng ₁ , Maolin Yuan ₁ , Ruixiang Li ₁ , Hua Chen ₁ , Haiyan Fu ₁

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Visible-light photoredox catalysis plays an important role in various reactions which are inaccessible under typical thermal conditions. Distinctly different from common visible-light photoredox catalysis which often involves transition-metal complexes, conjugated organic dyes, or electron donor–acceptor complexes, herein, the use of ion-pair charge-transfer (IPCT) complex-induced visible-light photoredox catalytic reactions are described, wherein the cyclization–methoxylation of N-vinyl amides in methanol was achieved under irradiation with blue LEDs. The reaction employs a heteroarenium iodide as the photocatalyst and can be extended to cyclization–alkoxylation, −acyloxylation, and −hydroxylation. This protocol provides an eco-friendly synthetic route to a wide range of oxazoline derivatives. Mechanistic investigations with UV–visible spectroscopy and control experiments confirm the existence of the IPCT absorption band in the visible region for the heteroarenium iodide, which is responsible for the observed reactivity.

中文翻译：

由离子对电荷转移络合物催化的 N-乙烯基酰胺的可见光诱导的恶唑啉形成

可见光光氧化还原催化在典型热条件下无法进行的各种反应中起着重要作用。与通常涉及过渡金属配合物、共轭有机染料或电子供体 - 受体配合物的常见可见光光氧化还原催化明显不同，此处使用离子对电荷转移 (IPCT) 配合物诱导可见光光氧化还原催化描述了反应，其中N的环化 - 甲氧基化- 乙烯酰胺甲醇溶液是在蓝光 LED 照射下获得的。该反应使用碘化杂芳烃作为光催化剂，并且可以扩展到环化-烷氧基化、-酰氧基化和-羟基化。该协议为各种恶唑啉衍生物提供了一种环保的合成路线。紫外-可见光谱和对照实验的机理研究证实了碘化杂芳烃在可见光区存在 IPCT 吸收带，这是观察到的反应性的原因。

更新日期：2021-09-17

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