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Synthesis 2024; 56(20): 3215-3219
DOI: 10.1055/a-2361-0069
DOI: 10.1055/a-2361-0069
paper
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
This work was supported by Grant-in-Aid for Scientific Research (Grant Number 20H02867) from the Japanese Society for the Promotion of Science (JSPS), the Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan; by a grant from the Naito Foundation; by a grant from the Yamada Science Foundation; and by a grant from the Research Grant of Institute of Natural Science at Nihon University for 2023.
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 under blue LED irradiation. Using this method, the allylic oxidation of dicyclopentadiene proceeded smoothly in air atmosphere with an 87% yield. The conditions, using TPP under blue LED irradiation, were expanded to include the oxidation of cyclopentadiene. The approach offers a simple and cost-effective method of synthesizing important building blocks for natural product synthesis.
Key words
5,10,15,20-tetraphenylporphyrin - blue LED - air atmosphere - singlet oxygen - dicyclopentadiene - cyclopentadieneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2361-0069.
- Supporting Information
Publikationsverlauf
Eingereicht: 25. Juni 2024
Angenommen nach Revision: 05. Juli 2024
Accepted Manuscript online:
05. Juli 2024
Artikel online veröffentlicht:
22. Juli 2024
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For selected allylic oxidation of dicyclopentadiene (1) using singlet oxygen, see:
For selected oxidation of cyclopentadiene (7) using rose bengal, see:
For specific instances demonstrating the generation of singlet oxygen using TPP and blue- or green-LED irradiation, see: