Photogenerated Azido Radical Mediated Oxidation: Access to Carbonyl Functionality from Alcohols, Alkylarenes, and Olefins via Organophotoredox,Advanced Synthesis & Catalysis

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Photogenerated Azido Radical Mediated Oxidation: Access to Carbonyl Functionality from Alcohols, Alkylarenes, and Olefins via Organophotoredox
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-10 , DOI: 10.1002/adsc.202200242
Maniklal Shee ₁ , N. D. Pradeep Singh ₁

Affiliation

Azido radical mediated photocatalytic oxidation method for the selective oxidation of various well-known feedstocks, such as (hetero)aromatic or aliphatic alcohols, alkylarenes, and terminal alkenes, is successfully accomplished. Herein, the catalytic HAT and reversible addition/elimination strategies of azido radical have been explored to convert the commonly oxidizable functionalities into invaluable carbonyls or tertiary alcohols using an organic photocatalyst 4CzIPN with tetrabutyl ammonium azide (TBAN₃) and air/O₂ as an oxidant. Indeed, this mild, operationally simple, and productive method offers good to excellent product yields with a wide range of structurally diverse substrates, including pharmaceutical derivatives with good functional group tolerance. Several control experiments have been carried out to investigate the detailed reaction mechanism.

中文翻译：

光生叠氮自由基介导的氧化：通过有机光氧化还原从醇、烷基芳烃和烯烃中获得羰基官能团

叠氮自由基介导的光催化氧化方法用于选择性氧化各种众所周知的原料，如（杂）芳族或脂肪族醇、烷基芳烃和末端烯烃，已成功完成。在此，已经探索了催化 HAT 和叠氮自由基的可逆添加/消除策略，以使用有机光催化剂 4CzIPN 与四丁基叠氮化铵 (TBAN ₃ ) 和空气/O _{2将常见的可氧化官能团转化为宝贵的羰基或叔醇。}作为氧化剂。事实上，这种温和、操作简单且高效的方法提供了良好至优异的产品产率，具有广泛的结构多样的底物，包括具有良好官能团耐受性的药物衍生物。已经进行了几个对照实验来研究详细的反应机理。

更新日期：2022-05-10

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