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Aerobic oxidative cleavage of CC bond to carbonyl compound
Results in Chemistry ( IF 2.5 ) Pub Date : 2021-05-05 , DOI: 10.1016/j.rechem.2021.100137
Long-Fei Jia , Huai-Zhu Li , Zhi-Hao Li , Rui-Jun Li , Guan-yu Yang

A highly efficient and selective carbon–carbon double bonds cleavage of styrene compounds involving molecular oxygen was achieved using TBHP as a free radical initiator in diethylene glycol diethyl ether medium. Various styrene compounds, such as phenyl acrylic acids and its esters, 2-substituted 3-phenyl acrylic acids and its esters, chalcones, 4-phenyl-3-buten-2-one and bis(2-phenylvinyl) ketone, 5-benzylidene-1,3-dimethyl-pyrimidine-2,4,6-triones, could be effectively oxidized into the corresponding aryl carbonyl compounds, and the yield was up to 99%. A suitable mechanism was proposed. Gram-level synthesis further illustrated the practicality of our method.



中文翻译:

C 双键C键与羰基化合物的好氧氧化裂解

使用TBHP作为二甘醇二乙醚介质中的自由基引发剂,可以高效,选择性地裂解涉及分子氧的苯乙烯化合物的碳-碳双键。各种苯乙烯化合物,例如苯基丙烯酸及其酯,2-取代的3-苯基丙烯酸及其酯,查耳酮,4-苯基-3-丁烯-2-酮和双(2-苯基乙烯基)酮,5-亚苄基-1,3-二甲基-嘧啶-2,4,6-三酮可有效地氧化成相应的芳基羰基化合物,收率可达99%。提出了一种合适的机制。克级合成进一步说明了我们方法的实用性。

更新日期:2021-05-14
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