光氧化还原催化烯烃和醛参与1,3-二酮的四原子骨架编辑

doi:10.1016/S1872-2067(25)64863-7

催化学报 ›› 2026, Vol. 82: 212-224.DOI: 10.1016/S1872-2067(25)64863-7

光氧化还原催化烯烃和醛参与1,3-二酮的四原子骨架编辑

王微^a, 陈彬^a, 李婷^a, 陈证楚^a, 袁雷^a, 付强^a, 韦思平^a^,^*(), 吴小锋^b^,^*(), 易东^a^,^*()

^a西南医科大学药学院, 泸州市绿色制药技术重点实验室, 四川泸州 646000
^b中国科学院大连化学物理研究所, 大连洁净能源国家实验室, 辽宁大连 116023

收稿日期:2025-07-15 接受日期:2025-09-09 出版日期:2026-03-18 发布日期:2026-03-05
通讯作者: * 电子信箱: yidong@swmu.edu.cn (易东),xwu2020@dicp.ac.cn (吴小锋),swei1225@swmu.edu.cn (韦思平).
基金资助:
四川省科技计划(2024NSFSC2100);国家自然科学基金(22171233);泸州市人民政府-西南医科大学科技战略合作项目(2023LZXNYDJ019)

Photoredox-catalyzed four-atom skeletal editing of 1,3-diketones with alkenes and aldehydes

Wei Wang^a, Bin Chen^a, Ting Li^a, Zhengchu Chen^a, Lei Yuan^a, Qiang Fu^a, Siping Wei^a^,^*(), Xiao-Feng Wu^b^,^*(), Dong Yi^a^,^*()

^aGreen Pharmaceutical Technology Key Laboratory of Luzhou City, School of Pharmacy, Southwest Medical University, Luzhou 646000, Sichuan, China
^bDalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2025-07-15 Accepted:2025-09-09 Online:2026-03-18 Published:2026-03-05
Contact: * E-mail: yidong@swmu.edu.cn (D. Yi),xwu2020@dicp.ac.cn (X.-F. Wu),swei1225@swmu.edu.cn (S. Wei).
Supported by:
Sichuan Science and Technology Program(2024NSFSC2100);National Natural Science Foundation of China(22171233);Science and Technology Strategic Cooperation Programs of Luzhou Municipal People's Government and Southwest Medical University(2023LZXNYDJ019)

摘要/Abstract

摘要：

碳-碳(C-C)键的断裂与重组是一种极具吸引力且富有挑战性的策略, 能以原子经济性和步骤经济性的方式高效构建复杂的高附加值分子. 目前, 1,3-二酮中C(CO)-C键的断裂和重组通过骨架编辑方法转化为其他方法难以获得的结构单元已有广泛的研究.

相比而言, 光化学策略仍是实现1,3-二酮骨架编辑最为高效温和的途径之一, 但目前仅实现了单个或两个原子插入单元的骨架编辑, 要想插入三个及以上原子却颇具挑战. 为了提供结构多样的、含有高比例sp³碳原子(Fsp³)的饱和化分子以满足不断增长的药物发现需求, 开发1,3-二酮选择性插入三个或多个原子的光化学骨架编辑方法具有重要的研究价值.

近年来, 可见光氧化还原催化由于具有反应条件温和、绿色环保、官能团兼容性高等优点, 已成为现代有机合成化学的重要发展方向. 本文提出了一种新颖高效的可见光氧化还原催化的1,3-二酮四原子骨架编辑方法——丙氧基插入反应, 该方法以优异的原子经济性、步骤经济性和氧化还原经济性实现了1,3-二酮高选择性重组为一类结构新颖的酰基化1,5-酮醇. 值得注意的是, 所插入的丙氧基单元(含三个sp³碳和一个氧原子)来源于两种简单易得的起始原料: 烯烃和醛. 该方法具有反应条件温和、官能团兼容性好以及可用于合成活性分子衍生物等特点. 更重要的是, 通过光催化合成酰基化1,5-酮醇/Lewis酸促进的Wagner-Meerwein重排的串联反应和光催化[2+2+2]环化/甲磺酰氯促进消除的串联反应, 分别实现了高附加值产物γ,δ-不饱和酮和二氢吡喃的快速构建. 此外, 通过自由基捕获实验、自由基钟实验、紫外-可见吸收光谱、荧光淬灭、循环伏安法及原位核磁共振表征等机理研究, 证明1,3-二酮自由基、苄基自由基、羰基自由基和内半缩酮中间体均为该反应的关键中间体, 并提出了与经典De Mayo反应不同的自由基-自由基交叉偶联/重排反应机理: 首先, 在Brönsted碱作用下, 1,3-二酮发生去质子化形成烯醇负离子, 随后还原淬灭激发态光催化剂产生1,3-二酮自由基, 与芳基烯烃发生区域选择性自由基加成反应得到苄基自由基. 与此同时, 还原态光催化剂通过质子耦合电子转移过程促进醛生成羰基自由基. 最后, 苄基自由基和羰基自由基经过自由基-自由基交叉偶联以及快速的分子内亲核加成生成内半缩酮, 其通过逆aldol反应实现了C-C键断裂, 最终得到目标产物酰基化1,5-酮醇.

综上, 本文以自由基-自由基交叉偶联/重排的串联反应路径, 丰富了C(CO)-C键骨架编辑的领域, 在温和条件下实现了1,3-二酮的高效高选择性转化为高附加值的1,5-酮醇类化合物, 阐明了涉及羰基自由基的反应机制, 为1,3-二酮的多组分插入反应的开发和应用提供了新思路.

关键词: C-C键断裂, 1,3-二酮, 光氧化还原催化, 1,5-酮醇, 烯烃, 醛

Abstract:

Cleavage and reassembly of C-C bonds is a fascinating and challenging strategy to forge complex high-value molecules in an atom- and step-efficient manner. Herein, we disclose a photoredox-catalyzed four-atom skeletal editing strategy, enabling highly selective reassembly of 1,3-diketones into architecturally distinct acylated 1,5-ketoalcohols with excellent atom, step, and redox economy. Notably, this propoxy insertion unit (i.e., three sp³-hybridized carbons and one oxygen atom) is derived from the other two simple and readily available starting materials (i.e., alkene and aldehyde). Experimental studies have elucidated the key intermediate (lactol) and reaction mechanism (radical-radical crossover cyclization/rearrangement), which are distinct from classical De Mayo reaction. More importantly, the rapid construction of high-value-added product γ,δ-unsaturated ketones and dihydropyrans is also achieved via photocatalytic synthesis of acylated 1,5-ketoalcohols/Lewis acid-promoted Wagner-Meerwein rearrangement cascade and photocatalytic formal [2+2+2] annulation/MsCl-promoted elimination cascade, respectively.

Key words: C-C bond cleavage, 1,3-Diketones, Photoredox catalysis, 1,5-Ketoalcohols, Alkenes, Aldehydes

王微, 陈彬, 李婷, 陈证楚, 袁雷, 付强, 韦思平, 吴小锋, 易东. 光氧化还原催化烯烃和醛参与1,3-二酮的四原子骨架编辑[J]. 催化学报, 2026, 82: 212-224.

Wei Wang, Bin Chen, Ting Li, Zhengchu Chen, Lei Yuan, Qiang Fu, Siping Wei, Xiao-Feng Wu, Dong Yi. Photoredox-catalyzed four-atom skeletal editing of 1,3-diketones with alkenes and aldehydes[J]. Chinese Journal of Catalysis, 2026, 82: 212-224.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(25)64863-7

https://www.cjcatal.com/CN/Y2026/V82/I3/212

图/表 6

Fig. 1. Catalytic skeletal editing strategies of 1,3-diketones.

Fig. 2. Optimization of the reaction conditions a,b. a Reaction conditions: 1 (0.15 mmol), 2 (0.15 mmol), 3 (0.1 mmol), Ir(p-F-ppy)3 (1 mol%), K3PO4 (10 mol%), DMF (1 mL), 30 W blue LEDs, argon atmosphere, r.t., 6 h. n.d. = not detected. bThe yield was determined by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard. cIsolated yields based on 3.

Fig. 3. Substrate scope investigation a. Reaction conditions: a aldehyde (0.45 mmol), styrene (0.45 mmol), 1,3-diketone (0.3 mmol), Ir(p-F-ppy)3 (1 mol%), K3PO4 (10 mol%), DMF (3 mL), 30 W blue LEDs, argon atmosphere, r.t., 6 h, in a sealed tube. b 3DPA2FBN instead of Ir(p-F-ppy)3. c K3PO4 (30 mol%). d fac-Ir(ppy)3 instead of Ir(p-F-ppy)3. e [Ir(dtbbpy)(ppy)2)]PF6 instead of Ir(p-F-ppy)3. f 4CzIPN instead of Ir(p-F-ppy)3. g NaOH instead of K3PO4.

Fig. 4. Late-stage derivatization of biologically relevant molecules. Reaction conditions: aldehyde (0.45 mmol), 1,1-diphenylethylene (0.45 mmol), acetylacetone (0.3 mmol), Ir(p-F-ppy)3 (1 mol%), K3PO4 (10 mol%), DMF (3 mL), 30 W blue LEDs, argon atmosphere, r.t., 6 h, in a sealed tube.

Fig. 5. Mechanistic investigations. (A) Radical inhibition experiment with a radical scavenger (TEMPO, DMPO, or DNB). (B) Radical-probing experiment I with (1-(2-phenylcyclopropyl)vinyl)benzene instead of 1,1-diphenylethylene 2. (C) Radical-probing experiment II with N-methylquinoxalin-2(1H)-one instead of 1,1-diphenylethylene 2. (D) Radical-probing experiment III with the addition of allyl sulfone. (E) UV-visible absorption spectrum. (F) Stern-Volmer quenching experiment. (G) Cyclic voltammetry measurement. (H) Photocatalyst evaluation with different triplet stale energies. (I) In situ 1H-NMR experiment. (J) Mechanistic proposal.

Fig. 6. Synthetic utility of the methodology. (A) Photocatalytic formal [2+2+2] annulation for synthesis of dihydropyrans. (B) Scale-up reaction and stream-down modifications. (C) Synthesis of γ,δ-unsaturated ketones via sequential rearrangements. aTsOH·H2O, MeOH, r.t. b Ph3PCH3Br, KOtBu, THF, 0 °C to r.t. c NBS, TsOH, DCM, r.t. d NaBH4, MeOH, 0 °C to r.t. e LiAlH4, THF, 0 °C to r.t. f MeOH/KOH, DMP, CH2Cl2, r.t. g NaOAc, NH2OH·HCl, MeOH, r.t. h TfOH, m-CPBA, CH2Cl2, r.t.

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光氧化还原催化烯烃和醛参与1,3-二酮的四原子骨架编辑

Photoredox-catalyzed four-atom skeletal editing of 1,3-diketones with alkenes and aldehydes

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