Photocatalytic C–H Activation with Alcohol as a Hydrogen Atom Transfer Agent in a 9-Fluorenone Based Metal–Organic Framework,ACS Applied Materials & Interfaces

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Photocatalytic C–H Activation with Alcohol as a Hydrogen Atom Transfer Agent in a 9-Fluorenone Based Metal–Organic Framework
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2021-05-27 , DOI: 10.1021/acsami.1c03098
Zhonghe Wang ₁ , Le Zeng ₁ , Cheng He ₁ , Chunying Duan ₁

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Hydrogen atom transfer (HAT) has become an attractive strategy for the activation of hydrocarbon feedstocks. Alcohols, as inexpensive and efficient hydrogen transfer reagents, have limited application in C–H functionalization due to the difficulty in the alkoxy radical acquisition. 9-Fluorenone moieties were incorporated into the metal–organic framework (MOF) as a photocatalyst; through the formation of hydrogen bonds between the carbonyl group of a ligand and alcohol, alkoxy radicals could be obtained by the visible-light-driven oxidation of 2,2,2-trichloroethanol via proton-coupled electron transfer (PCET). Effectively photocatalyzed intermolecular coupling reactions between phenyl vinyl sulfone and aldehyde or cyclic ether were realized through the HAT pathway. Compared to homogeneous catalysts, the heterogeneous MOF photocatalyst improved the catalytic efficiency and could be recycled at least five times. The microenvironment of the Zn-OFDC channel was beneficial for the formation of hydrogen bonds and stability of alkoxy radicals.

中文翻译：

9-芴酮基金属-有机骨架中醇作为氢原子转移剂的光催化C-H活化

氢原子转移 (HAT) 已成为活化烃原料的有吸引力的策略。醇作为廉价且高效的氢转移试剂，由于难以获得烷氧基自由基，因此在 C-H 官能化中的应用受到限制。9-芴酮部分作为光催化剂加入金属有机骨架（MOF）中；通过的配体和醇的羰基之间形成氢键，烷氧基可通过2,2,2-三氯乙醇的可见光驱动氧化而得到通过质子耦合电子转移 (PCET)。苯基乙烯基砜与醛或环醚之间的有效光催化分子间偶联反应是通过HAT途径实现的。与均相催化剂相比，非均相 MOF 光催化剂提高了催化效率，并且至少可以循环使用 5 次。Zn-OFDC 通道的微环境有利于氢键的形成和烷氧基自由基的稳定性。

更新日期：2021-06-09

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