作为碘化试剂的 PIDA：可见光诱导吡唑并[1,5-a]嘧啶及其他杂环戊烯的碘化反应。

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-11-04 DOI:10.1002/asia.202401101

Suvam Paul, Sourav Das, Tathagata Choudhuri, Papiya Sikdar, Avik Kumar Bagdi

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引用次数: 0

摘要

我们开发了一种在无光催化剂条件下利用二乙酰氧基碘苯（PIDA）进行杂环戊烯碘化的可见光介导的便捷高效策略。这种独特的方法是首次报道使用 PIDA 作为碘化剂进行光催化 C-H 碘化。新的无光催化剂策略适用于多种具有不同官能度的吡唑并[1,5-a]嘧啶衍生物。利用这种良性方案，还完成了其他富电子杂环的碘化，如咪唑并[1,2-a]吡啶、咪唑并[1,2-a]嘧啶、咪唑并[2,1-b]噻唑、苯并[d]咪唑并[2,1-b]噻唑和吡唑。3-iodo 吡唑并[1,5-a]嘧啶作为合成中间体在合成各种官能化吡唑并[1,5-a]嘧啶中的用途已得到证实。

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PIDA as an Iodinating Reagent: Visible-Light-Induced Iodination of Pyrazolo[1,5-a]pyrimidines and Other Heteroarenes.

We have developed a visible-light-mediated convenient and efficient strategy for the iodination of heteroarenes using diacetoxyiodobenzene (PIDA) under photocatalyst-free conditions. This unique approach is the first report on photocatalytic C-H iodination employing PIDA as the iodinating agent. The new photocatalyst-free strategy is applicable to a wide range of pyrazolo[1,5-a]pyrimidine derivatives with various functionalities. Iodination of other electron-rich heterocycles like imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, and pyrazoles has been accomplished employing this benign protocol. The usefulness of 3-iodo pyrazolo[1,5-a]pyrimidine as a synthetic intermediate in synthesizing various functionalized pyrazolo[1,5-a]pyrimidines has been demonstrated.

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).