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Transition Metal-Free Supramolecular Photoredox Catalysis in Water: A Phenoxazine Photocatalyst Encapsulated in V-Shaped Aromatic Amphiphiles
ACS Catalysis ( IF 12.9 ) Pub Date : 2020-11-23 , DOI: 10.1021/acscatal.0c04221
Naoki Noto 1 , Yuki Hyodo 1 , Michito Yoshizawa 1, 2 , Takashi Koike 1, 2 , Munetaka Akita 1, 2
Affiliation  

An organic reaction in water using visible light as the only energy source is one of the goals of modern synthetic organic chemistry, and the encapsulation of a photoredox catalyst by a water-soluble molecular capsule is a promising strategy for it. Herein, we report on a transition metal-free supramolecular catalyst composed of V-shaped aromatic amphiphiles and a phenoxazine photoredox catalyst. A nanosized molecular capsule can efficiently uptake an organic photoredox catalyst in water, and the supramolecular catalysis can be tuned by choice of the host–guest combination. This system allows for the effective reduction of organic molecules under visible light irradiation and generates various carbon-centered radicals, such as ketyl radicals, aryl radicals, and trifluoromethyl radicals, for organic reactions in water. In particular, the present supramolecular catalysis turns out to be effective for pinacol couplings compared to the photoredox catalysis in organic solvents, and furthermore, it enables recycling of the catalyst and substrate-selective reactions, which are difficult to be achieved by the conventional photoredox catalysis in organic solvents.

中文翻译:

水中无过渡金属的超分子光氧化还原催化:苯并恶嗪光催化剂包裹在V型芳香两亲物中。

使用可见光作为唯一能源的水中有机反应是现代合成有机化学的目标之一,用水溶性分子胶囊封装光氧化还原催化剂是一种有前途的策略。在本文中,我们报道了由V形芳香两亲物和苯恶嗪光氧化还原催化剂组成的无过渡金属的超分子催化剂。纳米分子胶囊可以有效地吸收水中的有机光氧化还原催化剂,超分子催化可以通过选择主客体组合来调节。该系统允许在可见光照射下有效还原有机分子,并产生各种以碳为中心的自由基,例如酮基,芳基和三氟甲基,用于水中的有机反应。尤其是,
更新日期:2020-12-04
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