半多相光催化经SO2插入的多组分串联环化反应: DDQ作为双功能氢转移/氧化还原催化剂用于2-炔基联芳烃合成磺酰基菲

doi:10.6023/A26090304

化学学报下一篇

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半多相光催化经SO₂插入的多组分串联环化反应: DDQ作为双功能氢转移/氧化还原催化剂用于2-炔基联芳烃合成磺酰基菲

张子彤^a#, 廖哲^a#, 胡丹露^a, 易荣楠^*b, 姜东方^c, 唐裕才^de, 王力立^*a, 何卫民^*a

^a南华大学化学化工学院衡阳 421001;
^b湖南警察学院食药环及毒品检验技术湖南省普通高等学校重点实验室长沙 410138;
^c长沙医学院功能核酸基础与临床湖南省普通高校重点实验室长沙 410219;
^d湖南文理学院化学与材料工程学院常德 415000;
^e南京林业大学化学工程学院南京 210037

投稿日期:2026-09-01
作者简介:^#共同第一作者
基金资助:
湖南省自然科学基金(No. 2026JJ90135) , 湖南省教育厅科学研究项目(No. 25A0703), 长沙市自然科学基金 (No.104872).

Semi‑Heterogeneous Photoredox‑Catalyzed SO₂‑Insertive Multicomponent Cascade Cyclization: DDQ as a Dual HAT/Redox Catalyst for Sulfonyl Phenanthrenes from 2‑Alkynyl Biaryls

Zi-Tong Zhang^a#, Zhe Liao^a#, Dan-Lu Hu^a, Rong-Nan Yi^b,*, Dong-Fang Jiang^c, Yu-Cai Tang^d,e, Li-Li Wang^a,*, Wei-Min He^a,*

^aSchool of Chemistry and Chemical Engineering, University of South China, Hengyang 421001;
^bKey Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138;
^cHunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219;
^dCollege of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde 415000;
^eSchool of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2026-09-01
Contact: * E-mail: yrn@hnu.edu.cn; wangll@usc.edu.cn; weiminhe@usc.edu.cn
About author:^#These authors contributed equally to this work
Supported by:
Hunan Provincial Natural Science Foundation (No. 2026JJ90135), the Scientific Research Fund of Hunan Provincial Education Department (No. 25A0703 and No.23B0411) and the Changsha Natural Science Foundation (No.104872)

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1. Supporting information-A26090304.pdf(3896KB)

摘要/Abstract

磺酰基菲类化合物广泛存在于生物活性分子与功能材料中, 其高效构建一直是有机合成化学的研究热点. 本文报道了一种由本征半导体光催化剂CW₂与有机小分子催化剂DDQ组成的半多相协同光催化体系, 在可见光照射及室温条件下, 成功实现了2-炔基联芳烃、Na₂S₂O₅与芳基重氮四氟硼酸盐经SO₂自由基插入的多组分串联磺酰化/环化反应, 以中等至良好的收率获得一系列磺酰基菲类化合物. 该反应具有条件温和、操作简便、官能团兼容性优异、易于放大以及光催化剂可高效循环利用等优势. 机理研究表明, 该反应经由自由基路径进行, 涉及SO₂插入、自由基加成及分子内环化等关键步骤. DDQ在反应中同时充当氢原子转移催化剂和氧化还原催化剂, 显著简化了催化体系. 本工作不仅为磺酰基菲类化合物的合成提供了一条简便绿色的新途径, 有望应用于药物化学与功能材料领域, 也为本征半导体光催化剂/有机小分子催化剂协同催化策略的发展提供了有益参考.

关键词: 可见光催化, 半导体光催化剂, 磺酰化反应, SO₂自由基插入, 菲

A semi-heterogeneous visible-light photocatalytic system has been developed for the direct construction of sulfonyl phenanthrenes via a multicomponent cascade sulfonylation/cyclization reaction. The protocol employs the inexpensive intrinsic semiconductor CW₂ as a heterogeneous photocatalyst and DDQ as a bifunctional homogeneous organocatalyst, enabling the efficient coupling of 2-alkynyl biaryls, Na₂S₂O₅ (as an inorganic SO₂ surrogate), and aryldiazonium tetrafluoroborates under mild conditions. This redox-mediator-assisted semiconductor photocatalysis effectively suppresses photogenerated electron-hole recombination and enhances interfacial charge transfer, thus overcoming the intrinsic limitations of conventional single-component semiconductor photocatalysis. The reaction exhibits broad substrate scope with respect to both coupling partners, delivering a wide range of sulfonyl phenanthrenes in good to excellent yields. Importantly, the catalyst system is scalable to gram-level synthesis, and the CW₂ photocatalyst can be readily recovered and reused without significant loss of activity. Mechanistic investigations reveal that DDQ plays a crucial dual role in the catalytic cycle: it acts as a HAT catalyst to facilitate phenanthrene ring formation, and simultaneously serves as a redox mediator to sustain the photocatalytic turnover of CW₂. This synergistic interplay between heterogeneous photon harvesting and homogeneous radical/redox mediation is the key to the high efficiency of the cascade process. The protocol offers distinct practical advantages, including the use of commercially available and low-cost catalysts, mild and operationally simple conditions, excellent functional-group tolerance, and catalyst recyclability. This dual-catalytic strategy provides a sustainable and versatile platform for the synthesis of valuable sulfonyl phenanthrenes, with promising potential for applications in medicinal chemistry and functional materials.

Key words: visible-light photocatalysis, semiconductor photocatalysis, sulfonylation reaction, SO₂insertion, phenanthrene

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张子彤, 廖哲, 胡丹露, 易荣楠, 姜东方, 唐裕才, 王力立, 何卫民. 半多相光催化经SO₂插入的多组分串联环化反应: DDQ作为双功能氢转移/氧化还原催化剂用于2-炔基联芳烃合成磺酰基菲[J]. 化学学报, doi: 10.6023/A26090304.

Zi-Tong Zhang, Zhe Liao, Dan-Lu Hu, Rong-Nan Yi, Dong-Fang Jiang, Yu-Cai Tang, Li-Li Wang, Wei-Min He. Semi‑Heterogeneous Photoredox‑Catalyzed SO₂‑Insertive Multicomponent Cascade Cyclization: DDQ as a Dual HAT/Redox Catalyst for Sulfonyl Phenanthrenes from 2‑Alkynyl Biaryls[J]. Acta Chimica Sinica, doi: 10.6023/A26090304.

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半多相光催化经SO₂插入的多组分串联环化反应: DDQ作为双功能氢转移/氧化还原催化剂用于2-炔基联芳烃合成磺酰基菲

Semi‑Heterogeneous Photoredox‑Catalyzed SO₂‑Insertive Multicomponent Cascade Cyclization: DDQ as a Dual HAT/Redox Catalyst for Sulfonyl Phenanthrenes from 2‑Alkynyl Biaryls

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