基于笼限域催化的(苯并)呋喃与激发态烯烃分子间不对称去芳构化光环加成反应

doi:10.1016/S1872-2067(26)65001-2

催化学报 ›› 2026, Vol. 85: 346-355.DOI: 10.1016/S1872-2067(26)65001-2

基于笼限域催化的(苯并)呋喃与激发态烯烃分子间不对称去芳构化光环加成反应

阮嘉, 陈文静, 李子谦, 胡鹏(), 苏成勇()

中山大学化学学院, 广东省高等学校功能分子工程基础研究卓越中心, 莱恩功能材料研究所, 绿色化学与分子工程研究院, 广东广州 510006

收稿日期:2025-08-15 接受日期:2025-12-06 出版日期:2026-06-18 发布日期:2026-05-18
通讯作者: *电子信箱: hupeng8@mail.sysu.edu.cn (胡鹏),
cesscy@mail.sysu.edu.cn (苏成勇).
基金资助:
国家重点研发计划(2021YFA1500401);中央高校青年教师科研创新能力支持项目(ZYGXQNJSKYCXNLZCXM-M28);国家自然科学基金(92461302);国家自然科学基金(22471298);广东省科学技术厅项目(2019QN01L151);广州市科学技术局项目(2025A04J7100);中央高校基本科研业务费专项资金

Intermolecular asymmetric dearomative photocycloaddition of (benzo)furans with excited alkenes via cage-confined catalysis

Jia Ruan, Wenjing Chen, Ziqian Li, Peng Hu(), Cheng-Yong Su()

GBRCE for Functional Molecular Engineering, LIFM, IGCME, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, Guangdong, China

Received:2025-08-15 Accepted:2025-12-06 Online:2026-06-18 Published:2026-05-18
Contact: *E-mail: hupeng8@mail.sysu.edu.cn (P. Hu),
cesscy@mail.sysu.edu.cn (C.-Y. Su).
Supported by:
NKRD Program of China(2021YFA1500401);Scientific Research Innovation Capability Support Project for Young Faculty(ZYGXQNJSKYCXNLZCXM-M28);NSFC Projects(92461302);NSFC Projects(22471298);Guangdong Provincial Department of Science and Technology(2019QN01L151);Guangzhou Municipal Science and Technology Bureau(2025A04J7100);FRF for the Central Universities

摘要/Abstract

摘要：

光环加成反应已成为一种强有力的去芳构化方法; 然而, 激发态烯烃与非光活性芳香族化合物的反应, 尤其分子间环加成的反应仍面临挑战. 此外, 不对称去芳构化光环加成反应的研究一直停滞不前. 催化不对称去芳构化反应能够将来源广泛的平面芳香化合物转化成结构复杂的三维手性分子, 因而在有机合成中受到化学家们的重视. 近年来, 可见光诱导Dexter能量传递的光环加成反应为去芳构化反应提供了一个特殊的平台, 但目前仍存在以下挑战: (1)基态的非光活性芳烃分子与激发态的光活性烯烃发生环加成发展仍十分有限; (2)不对称去芳构化光环加成的发展缓慢, 且有限的例子仍然需要特殊结构的底物, 以使基态的芳香化合物可以通过与手性催化剂形成配位键或氢键进行结合, 因此限制了底物与产物的结构多样性.

本研究通过笼限域光催化策略, 成功实现了激发态肉桂酸酯与非光活性(苯并)呋喃的分子间不对称去芳构化光环加成反应. 笼状空腔中的纳米限域化学空间可封装两个不同官能团取代底物, 进而实现高化学选择性、非对映选择性及对映选择性的不对称去芳构化反应, 为三维手性环状分子的合成提供了新路径. 本文使用具有钌光敏中心的金属-有机笼Δ/Λ-MOC-16作为手性光催化剂. 该笼催化剂可以通过主客体作用将肉桂酸酯类化合物与芳香化合物共封装在手性限域空腔中. 由于肉桂酸酯类化合物三重态能量较低, 而芳香化合物的三重态能量较高, 因此具有合适三重态能量的Δ/Λ-MOC-16可以通过能量传递的方式选择性激发肉桂酸酯类化合物, 进而与基态的芳香化合物发生分子间的不对称去芳构化环加成反应. 首先通过稳态Stern-Volmer荧光猝灭实验和紫外-可见吸收光谱证明了光催化剂Λ-MOC-16可以选择性地将三重态能量传递给肉桂酸酯化合物, 使其达到激发态, 从而在笼的手性限域空间内发生分子间的不对称去芳构化光环加成反应. 在得到最优的反应条件之后, 对两种底物的普适性进行了探索, 以最高99%的产率和99%ee的对映选择性合成得到了50个手性三维手性环状分子. 此外通过自由基抑制剂等对照实验、核磁滴定实验、增溶实验、高分辨质谱实验等, 揭示了Λ-MOC-16可以起到光敏催化中心、手性催化中心、加快反应速率、提高不同底物共封装率等多重作用.

综上, 本工作利用手性金属有机笼实现了光活性肉桂酸酯和非光活性(苯并)呋喃的分子间[2+2]不对称去芳构化光环加成反应. 本策略可以广泛兼容不同的官能团, 并产生结构丰富的三维稠环骨架. 该仿生笼状催化剂有力补充了去芳构化光环加成的反应类型, 也拓展了高效光催化不对称去芳构化的平台.

关键词: 不对称光催化, 不对称去芳构化, [2+2]光环加成, 仿生催化, 金属-有机笼

Abstract:

Photocycloaddition has recently emerged as a powerful dearomatization method; however, there is a challenge in the reaction between excited alkenes and non-photoactive aromatics, particularly for intermolecular cycloaddition. Moreover, advancements in asymmetric dearomative photocycloaddition have remained stagnant. In this study, we present an efficient approach to achieve intermolecular asymmetric dearomative photocycloaddition between excited cinnamates and non-photoactive (benzo)furans by virtue of cage-confined photocatalysis. The nanoconfined chemical spaces in cage-pockets facilitate heteromolecular co-encapsulation of substrates carrying variable functional groups, promoting efficient asymmetric dearomatization in high levels of chemo-, diastereo-, and enantioselectivity for the synthesis of three-dimensional chiral cyclic molecules.

Key words: Asymmetric photocatalysis, Asymmetric dearomatization, [2+2] Photocycloaddition, Biomimic catalysis, Metal-organic cage

阮嘉, 陈文静, 李子谦, 胡鹏, 苏成勇. 基于笼限域催化的(苯并)呋喃与激发态烯烃分子间不对称去芳构化光环加成反应[J]. 催化学报, 2026, 85: 346-355.

Jia Ruan, Wenjing Chen, Ziqian Li, Peng Hu, Cheng-Yong Su. Intermolecular asymmetric dearomative photocycloaddition of (benzo)furans with excited alkenes via cage-confined catalysis[J]. Chinese Journal of Catalysis, 2026, 85: 346-355.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(26)65001-2

https://www.cjcatal.com/CN/Y2026/V85/I6/346

图/表 6

Fig. 1. Strategies for dearomative photocycloadition. (a) Previous strategies of dearomative photocycloaddition for different types of aromatics and alkenes. (b) Representative works for ADAPCs in catalytic fashion. (c) Intermolecular ADAPC with photoactive alkenes by cage-confined chiral-pockets of the artificial enzymatic photoreactor Λ-MOC-16 (Δ-MOC-16 produces opposite enantiomer).

Fig. 2. Initial studies. (a) 1a (0.2 mmol), 1b (0.1 mmol), 0.5 mol% Λ-MOC-16 and DMSO:H2O (1:3, 3 mL) were stirred under N2 for 24 h with white LEDs as the light source. (b) Stern-Volmer quenching plot of Λ-MOC-16 with 1a or 1b in DMSO: H2O (1: 3). Quenching rate Ksv(1a) = 1370 L/mol, Ksv(1b) = 186 L/mol. (c) UV-vis spectra of 1a (1 × 10-4 mol/L), 1b (1 × 10-4 mol/L), MOC-16 (1 × 10-5 mol/L) in mixed solvent (DMSO:H2O = 1:3, v:v), and normalized emission spectrum of white LEDs.

Table 1 Optimization study.

Entry	Solvent	Conversion of 1a^a (%)	Conversion of 1b^a(%)	Yield of 1 (d.r.)^a (%)	ee of 1^b (%)
1	DMSO:H₂O = 1:3, 3 mL	92	78	45 (10.5:1)	90
2	DMF:H₂O = 1:3, 3 mL	76	90	73 (4.7:1)	87
3	MeOH H₂O = 1:3, 3 mL	98	89	69 (5.5:1)	84
4	THF:H₂O = 1:3, 3 mL	88	58	42 (3.6:1)	76
5	Acetone:H₂O = 1:3, 3 mL	98	86	72 (5.2:1)	86
6	NMP:H₂O = 1:3, 3 mL	76	87	66 (4.9:1)	83
7	MeCN:H₂O = 1:3, 3 mL	>99	84	71 (6.2:1)	84
8	H₂O, 3 mL	71	52	37 (3.9:1)	88
9	DMSO:H₂O = 1:4, 3 mL	72	74	52 (6.1:1)	91
10	DMSO:H₂O:MeOH = 1:4:3, 4.8 mL	92	>99	94, 90^c(5.4:1)	90
11^d	DMSO:H₂O:MeOH = 1:4:3, 4.8 mL	5	21	trace	—
12^e	DMSO:H₂O:MeOH = 1:4:3, 4.8 mL	—	—	n.r.	—

Fig. 3. Substrate scope of (benzo)furans. Reaction conditions: A mixture of 1a (2 equiv., 0.2 mmol) and 1b-29b (1 equiv., 0.1 mmol), 0.5 mol% Λ-MOC-16, and solvent (4.8 mL, DMSO:H2O:MeOH = 1:4:3) was stirred under N2 for 12-36 h with white LEDs as light source. Isolated yields are shown. Diastereomer ratios (d.r.) were determined by 1H NMR analysis of the crude reaction mixture. Enantiomeric excess (ee) ratios were determined using high performance liquid chromatography (HPLC) analysis. Single-crystal structures of an enantiomeric pair of 10 and 11 as well as 30 are shown in SI. a 0.5 mol% Δ-MOC-16. b3 mmol scale, 56 h.

Fig. 4. Substrate scope of cinnamates and transformation study. Reaction conditions: A mixture of 2a-21a (2 equiv., 0.2 mmol) and 7b (1 equiv., 0.1 mmol), 0.5 mol% Λ-MOC-16, and solvent (4.8 mL, DMSO: H2O: MeOH = 1: 4: 3) was stirred under N2 for 24 h with white LEDs as the light source. Isolated yields are shown. Diastereomer ratios (d.r.) were determined by 1H NMR analysis of the crude reaction mixture. Enantiomeric excess (e.e.) ratios were determined using HPLC analysis. a4 mmol scale, 60 h. Transformation of 36: a, LiOH·H2O, THF/MeOH (2:1), 0 °C; b, LiHMDS, THF, -78 °C; c, 4-methoxyphenylboronic acid, Pd(PPh3)4, Na2CO3, toluene, 80 °C; d, trimethylsilylacetylene, Pd(PPh3)2Cl2, PPh3, CuI, triethylamine, 70 °C.

Fig. 5. Host-guest chemistry and catalytic study. (a) Control experiments between 1a and 7b. Standard conditions: 0.5 mol% Λ-MOC-16, under N2, at room temperature for 16 h, 1a:7b = 2:1, 1 equiv. = 0.1 mmol, DMSO: H2O: MeOH = 1:4:3 (v:v, 4.8 mL), 4 × 5 W white LEDs as light source. aConversion of substrates and yield of products were analyzed by 1H NMR yields of crude products. bEnantiomeric excess (ee) determined by chiral HPLC. (b) Solubilization enhancing effect of MOC-16 (1.04 × 10-4 mol/L) to improve solubilities of representative substrates in aqueous solvent (DMSO: H2O: MeOH = 1:4:3) via phase-transfer driven by host-inclusion. (c) Co-solubility of different substrates (1a + 7b) in solvent (DMSO: H2O: MeOH = 1:4:) with or without MOC-16 (1.04 × 10-4 mol/L). (d) Titration curve fitting with Hill function of 1a and 7b (400 MHz, DMSO-d6: CD3OD: D2O = 1:3:4, v:v:v, 298 K). (e) 1H NMR titration 7b (1-13 equiv.) into a [1a]7⊂MOC-16 host-guest system (400 MHz, DMSO-d6: CD3OD: D2O = 1:3:4, v:v:v, 298 K), showing co-encapsulation of these two different substrates. The proton signals of MOC-16, 1a and 7b are labeled as black, orange and green dots, respectively.

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基于笼限域催化的(苯并)呋喃与激发态烯烃分子间不对称去芳构化光环加成反应

Intermolecular asymmetric dearomative photocycloaddition of (benzo)furans with excited alkenes via cage-confined catalysis

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[1]	田栋, 孙鑫, 曹珊珊, 王二萌, 尹艳丽, 赵筱薇, 江智勇. 乙烯基氮杂芳烃参与的不对称分子间[2 + 2]光环加成反应[J]. 催化学报, 2022, 43(10): 2732-2742.
[2]	王原溥, 刘靓, 吴东俊, 郭靖, 石建英, 刘军民, 苏成勇. 金属-有机分子笼在g-C₃N₄半导体上的固定以提高光催化产氢性能[J]. 催化学报, 2019, 40(8): 1198-1204.