Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl acrylamides through consecutive photoinduced electron transfer,Green Chemistry

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Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl acrylamides through consecutive photoinduced electron transfer
Green Chemistry ( IF 9.3 ) Pub Date : 2022-07-13 , DOI: 10.1039/d2gc01966c
Zhonghua Qu ₁ , Tong Tian ₁ , Yongbo Tan ₁ , Xiaochen Ji ₁ , Guo-Jun Deng _{1,

2} , Huawen Huang _{1,

2}

Affiliation

While the reductive ketyl couplings of carbonyls have been widely explored, we report in this work on a redox-neutral umpolung carbonyl coupling reaction through ketyl radical formation by consecutive photoinduced electron transfer (ConPET) under metal- and additive-free conditions. The donor–acceptor cyanoarene-based fluorophore, 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), was used as an efficient photocatalyst. It undergoes ConPET to form the excited radical anion (4CzIPN˙⁻*) possessing high reductive potential without an external electron donor. This mild and simple photocatalytic system allows highly efficient coupling/cyclization of N-aryl acrylamides and carbonyls and provides straightforward access to structurally useful hydroxyalkyl oxindoles with formal 100% atom economy.

中文翻译：

通过连续光诱导电子转移实现羰基与 N-芳基丙烯酰胺的氧化还原中性酮基自由基偶联/环化

虽然羰基的还原性酮基偶联已被广泛探索，但我们在这项工作中报告了在无金属和无添加剂条件下通过连续光诱导电子转移 (ConPET) 形成酮基自由基的氧化还原中性 umpolung 羰基偶联反应。供体-受体氰基芳烃基荧光团 1,2,3,5-四（咔唑-9-基）-4,6-二氰基苯（4CzIPN）被用作高效的光催化剂。它经过ConPET形成具有高还原电位的激发自由基阴离子（4CzIPN˙ ^- *），无需外部电子供体。这种温和而简单的光催化系统可实现N的高效偶联/环化-芳基丙烯酰胺和羰基化合物，并提供直接获得结构上有用的羟烷基羟吲哚的途径，并具有正式的 100% 原子经济性。

更新日期：2022-07-13

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