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Selenium-incorporated polymeric carbon nitride for visible-light photocatalytic regio-specific epoxidation of β-ionone
Molecular Catalysis ( IF 3.9 ) Pub Date : 2019-11-22 , DOI: 10.1016/j.mcat.2019.110715
Hongjia Li , Hongen Cao , Tian Chen , Xu Zhang , Yaocheng Shi

Selenium-incorporated polymeric carbon nitride (PCN)-catalyzed epoxidation reaction of β-ionone was developed for producing (E)-4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)but-3-en-2-one, which was a popular spice in perfume production as well as the key intermediate for the total synthesis of the highly demanded phytohormone abscisic acid. The reaction employed water as cheap, safe and green precursor of H2O2 oxidant and utilized visible light as the driving force. It was found that introducing Se into the material from Se powder significantly enhanced the catalytic activity of PCN owing to the predominantly increased specific surface area of the catalyst (37.7 m²/g of PCN-Se vs. 16.6 m²/g of simple PCN) and the oxygen carrier catalyst features of incorporated Se. The highly electropositive Se sites facilitated their electrophilic additions with the thermodynamically unfavourable endocyclic C=C of β-ionone, affording a regio-specific access to useful epoxide product. This is the first report of the unique PCN-Se relay catalysis procedure.



中文翻译:

掺硒的聚合氮化碳,用于β-紫罗兰酮的可见光光催化区域特异性环氧化

开发了掺硒的高分子氮化碳(PCN)催化的β-紫罗兰酮的环氧化反应,以生产(E)-4-(2,2,6-三甲基-7-氧杂双环[4.1.0]庚-1-基) but-3-en-2-one,它是香水生产中流行的香料,也是高度需求的植物激素脱落酸全合成的关键中间体。反应使用水作为H 2 O 2的廉价,安全和绿色前体氧化剂并利用可见光作为驱动力。结果发现,由于主要增加了催化剂的比表面积(37.7m²/ g PCN-Se相对于16.6m²/ g简单PCN),从Se粉中将Se引入材料中显着提高了PCN的催化活性。掺入硒的氧载体催化剂的特点 高度电正性的Se位点促进了它们的亲电加成,而β-紫罗兰酮的热力学不利的环内C = C ,从而提供了对特定环氧基的有用环氧产物的途径。这是独特的PCN-Se中继催化程序的第一份报告。

更新日期:2019-11-26
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