Efficient Oxidation with Singlet Oxygen from 5,10,15,20-Tetraphenylporphyrin under Blue LED Irradiation and Air Atmosphere: Simplified Preparation of Key Building Blocks for Natural Product Synthesis

Synthesis Pub Date : 2024-07-05 DOI:10.1055/a-2361-0069
Masato Hasumi, Tomohiro Tsutsumi, Daiki Shikama, Ichiro Hayakawa
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Abstract

A method for preparing important building blocks for natural product synthesis has been developed using singlet oxygen generated from 5,10,15,20-tetraphenylporphyrin (TPP) under blue LED irradiation. Using this method, the allylic oxidation of dicyclopentadiene proceeded smoothly in air atmosphere with an 87% yield. This condition, using TPP under blue LED irradiation, was expanded to include the oxidation of cyclopentadiene. It is a simple and cost-effective method of synthesizing important building blocks for natural product synthesis.

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在蓝光 LED 照射和空气环境下,5,10,15,20-四苯基卟啉与单线态氧的高效氧化:简化天然产物合成关键组分的制备过程
在蓝光 LED 的照射下,利用 5、10、15、20-四苯基卟啉(TPP)产生的单线态氧,开发出了一种用于制备天然产物合成的重要构筑物的方法。利用这种方法,二环戊二烯的烯丙基氧化反应在空气中顺利进行,产率达 87%。在蓝光 LED 的照射下使用 TPP 的这一条件被扩展到环戊二烯的氧化。这是一种简单而经济有效的方法,可用于合成天然产物的重要构筑物。
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