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Synchronized biphotonic process triggering CC coupling catalytic reactions
Applied Catalysis B: Environment and Energy ( IF 22.1 ) Pub Date : 2018-05-22 , DOI: 10.1016/j.apcatb.2018.05.062
Carmen G. López-Calixto , Marta Liras , Victor A. de la Peña O’Shea , Raúl Pérez-Ruiz

Activation of aryl(Ar)-halides for CC coupling catalytic reactions using visible light has become one of the most challenging tasks in organic synthesis since it offers effective and safer alternatives to traditional dehalogenation protocols. The insufficient energy provided by visible light to cleave such strong CH alogen bonds certainly makes necessary the development of new protocols to overcome this limitation. We report here the application of photon upconversion (UC) technology based on triplet-triplet annihilation (TTA) to a CC coupling catalytic reaction, a possibility that has not been investigated to date. This synchronized biphotonic process (TTA-UC) activates successfully Ar-halides with visible light. Based on product analysis and spectroscopic experiments, a cascade process combining photophysical and photochemical steps is proposed for the mechanism rationalization. Visible light, ambient temperature and pressure, low-loading metal-free photocatalysts and no additives make this protocol very attractive for applications to the synthesis of fine chemical building blocks, pharmaceuticals, agrochemicals or new materials.



中文翻译:

同步双光子过程触发C C耦合催化反应

使用可见光活化芳基(Ar)-卤化物进行C C偶联催化反应已成为有机合成中最具挑战性的任务之一,因为它提供了传统脱卤方案的有效且更安全的替代方法。可见光所提供的能量不足以切割这种强C H氢键,这无疑使得有必要开发新的方案来克服这一局限性。我们在此报告基于三重态三重态an灭(TTA)的光子上转换(UC)技术在C上的应用C偶联催化反应,迄今为止尚未研究的可能性。该同步双光子过程(TTA-UC)用可见光成功激活了卤化氩。基于产物分析和光谱实验,提出了将光物理和光化学步骤相结合的级联过程,以实现机理的合理化。可见光,环境温度和压力,低负荷,不含金属的光催化剂以及无添加剂,使得该协议非常适合用于精细化工构件,药物,农用化学品或新材料的合成。

更新日期:2018-05-22
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