Tailoring photocatalysts to modulate oxidative potential of anilides enhances para-selective electrochemical hydroxylation

Jianye Zhang, Zhaoliang Yang (), Chunlei Liu, Hao Wan, Zizhao Hao, Xinrui Ji, Pengjie Wang, Hong Yi () and Aiwen Lei ()
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Jianye Zhang: Jiangxi Normal University
Zhaoliang Yang: Jiangxi Normal University
Chunlei Liu: Jiangxi Normal University
Hao Wan: Jiangxi Normal University
Zizhao Hao: Jiangxi Normal University
Xinrui Ji: Jiangxi Normal University
Pengjie Wang: Wuhan University
Hong Yi: Wuhan University
Aiwen Lei: Jiangxi Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Phenolic compounds have long captivated the interest of organic synthesis, particularly in their quest for selective hydroxylation of arenes using H2O as a hydroxyl source. However, the inherent high reactivity and low redox potential of phenols often lead to undesirable overoxidation byproducts. To address this challenge, herein, we develop an electrophotochemical approach, finetuning substrate oxidative potential and enabling para-selective hydroxylation of anilides. This method showcases versatility, accommodating a wide array of substrates, while revealing high regional selectivity and compatibility with diverse functional groups. Moreover, the protocol allows facile late-stage functionalization of biologically active molecules. Mechanistic investigations demonstrate the activation of anilides by the excited state photocatalyst, effectively decreasing their oxidative potential and enhancing regional selectivity during hydroxylation. By using this protocol, important drug molecules such as Paracetamol, Fenretinide, Practolol, and AM404 could be synthesized, demonstrating the applicability of this approach in drug synthesis and late-stage functionalization.

Date: 2024
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DOI: 10.1038/s41467-024-51327-4

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