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2025 25020057

DOI: https://doi.org/10.6023/A25020057

Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives

  • Zhao Yu ,
  • Xing Tongtong ,
  • Duan Yurong ,
  • Zhao Quanqing
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  • aCollege of Chemistry and Chemical Engineeringt, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Yan'an, Shaanxi 716000, China;
    bJiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, College of Pharmacy, Jiangsu Ocean University, Lianyungang, Jiangsu, 222005

Received date: 2025-02-27

  Online published: 2025-04-24

Supported by

National Natural Science Foundation of China (Nos. 22161047, 22301109), the Research Funds for Talent Introduction of Jiangsu Ocean University (No. KQ23065) and Lianyungang Haiyan Project (No. KK24005) for support of this research.

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Abstract

Alcohols are the most wildly existent in nature, and one of promising chemical feedstocks, due to their cheap and easy availability. Half a century ago, the Barton-McCombie deoxygenation was discovered, and continued to be improved by organic synthetic chemists, becoming an important and rather broad fields in modern organic chemistry. In the last decade, visible-light-driven photoredox catalysis is a powerful tool in organic synthesis, and can realize a good deal of chemical transformations, because of its milder reaction condition, functional group tolerance, high efficiency and environmental-friendly characteristics. It has been reported direct deoxygenation of alcohol in the previous literatures, including the photochemical reactions and metal-transition catalytic systems. Herein, we summaried and discussed some significant advances since in 2014, about the deoxygenative functionalization of alcohol derivatives in photochemical synthetic reactions. And oxygen-containing derivatives of alcohol mainly includes carboxylic esters, oxalic esters, thiocarbonates and their derivatives, ethers and others. In this minireview, in terms of their structural properities, we went to classify and introduce the catalytic modes and mechanisms of deoxygenation, reaction universalities, advantages and shortcomings. In these advances, the oxygen-containing derivatives of alcohol could proceed single electron oxidation and reduction processes, hydrogen atom transfer (HAT), as well as radical addition process, as to assist the C–O bond cleavage to yield the key alkyl radical intermediates, subsequent functionalization to construct the newly C–C, C–N, C–O, C–S, C–X (halo) and C–B bonds. In addition, we also outlooked the challenges and opportunities in the field of deoxygenation of alcohols, and the application prospects of some compounds containing the hydroxy group in the future was discussed as well.

Key words： Deoxygenation of alcohol; Photochemical reactions; Oxygen-containing derivatives of alcohol; Deoxygenative functionalization

Cite this article

Zhao Yu , Xing Tongtong , Duan Yurong , Zhao Quanqing . Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives[J]. Acta Chimica Sinica, 2025 : 25020057 . DOI: 10.6023/A25020057

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