氰基乙烯类化合物的制备与应用研究进展

doi:10.6023/cjoc20203013

摘要/Abstract

氰基乙烯类是一类较易制备的π-π共轭化合物, 可通过Knoevenagel缩合反应、多组分反应、串联反应等绿色化方法获得. 氰基乙烯类中的特殊D-π-A类结构单元, 使其光学性质可应用于荧光探针、染料敏化电池中的敏化剂等领域. 同时, 氰基乙烯类化合物中β-位碳、氰基碳、γ-位碳电子云密度的不同影响着它们的化学反应性质, 使其可作为不同的合成子, 通过Michael加成型和环加成型等反应, 较温和地构建各种含氮化合物, 特别是环状化合物. 以合成氰基乙烯类化合物的类型为依据, 总结了其常见的制备策略; 按照在不同光学领域的应用, 介绍了氰基乙烯型荧光探针和电池敏化剂; 按照反应类型和产物结构, 综述了近年来其在有机合成领域的应用. 展望未来, 人们将会对其性能与应用有更多的了解, 设计更多性能优异的荧光探针分子, 同时深入发展氰基乙烯类化合物的有机合成应用.

关键词: 氰基乙烯, 荧光探针, 合成子, Michael加成型反应, 环加成型反应

Cyanoethylenes are a class of easily prepared π-π conjugated compounds, which can be obtained by Knoevenagel condensation, multi-component reaction, tandem reaction and other green methods. The special D-π-A structural unit in cyanoethylene compounds makes their optical properties applicable to the fields such as fluorescent probes, sensitizers in dye-sensitized batteries, etc. At the same time, the difference in the electron cloud density of β-carbon, cyanocarbon, and γ-carbon in cyanoethylenes affects their chemical reaction properties, so that they can be used as different synthons to mildly construct various nitrogen-containing compounds, especially cyclic compounds through Michael type addition and cycloaddition type reactions. Based on the types of cyanoethylene compounds, their common preparation strategies are summarized. According to the applications in different optical fields, cyanoethylene-type fluorescent probes and battery sensitizers are introduced. The applications of cyanoethylenes in the area of organic synthesis in recent years are also reviewed in accordance with the reaction type and product structure. In the future, with the more understanding of the performance and application of cyanoethylenes, the more fluorescent probe molecules with excellent performance will be designed, and the further organic synthesis application of cyanoethylene compounds will be developed.

Key words: cyanoethylene, fluorescent probe, synthon, Michael type addition, cycloaddition type reaction

引用此文

曾玉, 黎忠昊, 邓思威, 陈祖佳, 陈璧瑜, 宇世伟, 沈晴, 汪朝阳. 氰基乙烯类化合物的制备与应用研究进展[J]. 有机化学, 2024, 44(9): 2722-2731.

Yu Zeng, Zhonghao Li, Siwei Deng, Zujia Chen, Biyu Chen, Shiwei Yu, Qing Shen, Zhaoyang Wang. Research Progress on Preparation and Application of Cyanoethylenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2722-2731.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 11

图式1. 二氨基马来腈生成化合物3和4的合成反应

Scheme 1. Synthesis reaction of compounds 3 and 4 from diaminomaleonitrile

图式2. 探针5的合成与检测机理

Scheme 2. Synthesis and detection mechanism of probe 5

图式3. 探针6的合成与检测机理

Scheme 3. Synthesis and detection mechanism of probe 6

图式4. 探针7的合成与检测机理

Scheme 4. Synthesis and detection mechanism of probe 7

图1. 含有D-π-A类结构的荧光探针和荧光染料

Figure 1. Fluorescent probes and dyes containing D-π-A structures

图式5. 各种醛与β-取代α-氰基α,β-不饱和酯生成3,4,5-三取代哌啶的合成反应

Scheme 5. Synthesis of 3,4,5-trisubstituted piperidines from various aldehydes and β-substituted α-cyano α,β-unsaturated esters

图式6. 丙烯腈与芳基乙腈的Michael加成/分子内缩合级联反应

Scheme 6. Michael addition/intramolecular condensation cascade reaction of acrylonitrile with arylacetonitriles

图式7. 2-羟基肉桂醛与α,α-二氰基烯烃生成产物11的合成反应与反应机理

Scheme 7. Synthesis and reaction mechanism of product 11 from 2-hydroxycinnamaldehyde and α,α-dicyanoolefin

图式8. 二氰基烯烃与三氟重氮乙烷的[3＋2]环加成构建五元杂环

Scheme 8. [3＋2] cycloaddition of dicyanoalkenes with trifluorodiazoethane to construct a five-membered heterocyclic ring

图式9. 二氰基吡喃酮与NaN3的[3＋2]环加成反应

Scheme 9. [3＋2] cycloaddition reaction of dicyanopyrone with NaN3

图式10. 氧代单氰基烯与异腈生成3-酰基吡咯化合物的合成反应

Scheme 10. Synthesis of 3-acylpyrrole compounds by the reaction of oxygenated monocyanoalkenes with isocyanides

参考文献 118

[1]	Chen, M. Y.; Liang, Y. C.; Dong, T. T.; Liang, W. J.; Liu, Y. P.; Zhang, Y. G.; Huang, X.; Kong, L. C.; Wang, Z.-X.; Peng, B. Angew. Chem. Int. Ed. 2021, 60, 2339.
[2]	Ji, J.-M.; Zhou, H. R.; Eom, Y. K.; Kim, C. H.; Kim, H. K. Adv. Energy Mater. 2020, 10, 2000124.
[3]	Zeng, Q.; Chen, Y. M.; Yan, Y. Y.; Wan, R.; Li, Y. J.; Fu, H. L.; Liu, Y.; Liu, S.; Yan, X.-X.; Cui, M. C. Anal. Chem. 2022, 94, 15261.
[4]	Zagata, A.; Traskovskis, K.; Belyakov, S.; Mihailovs, I.; Bundulis, A.; Rutkis, M. Dyes Pigm. 2022, 208, 110864.
[5]	Ye, H.; Ke, Y. J.; Li, W. L.; Zhu, B. T.; Jiang, L. R.; Hu, X. C.; Zeng, L. T. Anal. Chim. Acta 2023, 1254, 341125.
[6]	Kleine-Kleffmann, L.; Schulz, A.; Stepanenko, V.; Würthner, F. Angew. Chem. Int. Ed. 2024, 62, e202314667.
[7]	Wang, J. Q; Wang, C. Y; Wang, Y. F; Qiao, J. W; Ren, J. Z; Li, J. Y; Wang, W. X.; Chen, Z. H; Yu, Y.; Hao, X. T; Zhang, S. Q; Hou, J. H. Angew. Chem. Int. Ed. 2024, 63, e20240056.
[8]	Duan, Z. Q.; Liu, M.; Zheng, B.; Tang, Y.; Du, J.; Wang, L.; Yu, S. C.; Wu, Y. J.; Guo, H. C. Org. Lett. 2023, 25, 3298.
[9]	Hu, C.-X.; Chen, L.; Hu, D.; Song, X.; Chen, Z.-C.; Du, W.; Chen, Y.-C. Org. Lett. 2022, 22, 8973.
[10]	Gao, C.-F.; Zhou, Y.; Ma, H.; Zhang, Y.; Nie, J.; Zhang, F.-G.; Ma, J.-A. CCS Chem. 2022, 4, 3693.
[11]	Gaviña, D.; Escolano, M.; Sotorríos, L.; Gómez-Bengoa, E.; López- Ortiz, F.; Sánchez-Roselló, M.; Pozo, C. D. Adv. Synth. Catal. 2023, 365, 1.
[12]	Chen, H.; Sun, S. H.; Liu, Y. A.; Liao, X. B. ACS Catal. 2020, 10, 1397.
[13]	Park, J.; Kim, T.-I.; Cho, S.; Pandith, A.; Kim, Y. Biomaterials 2022, 289, 121749.
[14]	Wang, K.; Lin, X. F.; Li, Q.; Liu, Y.; Li, C. Chin. J. Catal. 2022, 43, 1812. doi: 10.1016/S1872-2067(21)64051-2
[15]	Curti, C.; Battistini, L.; Sartori, A.; Zanardi, F. Chem. Rev. 2020, 120, 2448.
[16]	Cui, H. L.; Chen, Y. C. Chem. Commun. 2009, 30, 4479.
[17]	Mu, Y. C.; Nguyen, T. T.; Koh, M. J.; Schrock, R. R.; Hoveyda, A. H. Nat. Chem. 2019, 11, 478.
[18]	Shcherban, N. D.; Mäki-Arvela, P.; Aho, A.; Sergiienko, S. A.; Yaremov, P. S.; Eränen, K.; Murzin, D.Y. Catal. Sci. Technol. 2018, 8, 2928.
[19]	Gui, Q.-W.; Teng, F.; Li, Z.-C.; Jin, X.-F.; Zhang, M.; Dai, J.-N.; Lin, Y. W.; Cao, Z.; He, W. M. Org. Chem. Front. 2020, 7, 4026.
[20]	Miao, Z. C.; Luan, Y.; Qi, C.; Ramella, D. Dalton Trans. 2016, 45, 13917.
[21]	Meng, D.; Qiao, Y. S.; Wang, X.; Wen, W.; Zhao, S. H. RSC Adv. 2018, 8, 30180.
[22]	Nguyen, B. N.; Tran, M. H.; Bui, T. T. T.; Mac, D. H.; Pham, V.; Retailleau, P.; Nguyen, T. B. J. Org. Chem. 2023, 88, 11197.
[23]	Mydlova, L.; Taboukhat, S.; Waszkowska, K.; Ibrahim, N.; Migalska- Zalas, A.; Sahraoui, B.; Frère, P.; Makowska-Janusik, M. J. Mol. Liq. 2020, 314, 113622.
[24]	Yang, L.; Chen, S. Y.; Yi, D.; Chen, Q. X.; Zhang, J.; Xie, Y. S.; Sun, H. Y. J. Mater. Chem. B 2021, 9, 8512. doi: 10.1039/d1tb01189h pmid: 34554170
[25]	Anbu, N.; Maheswari, R.; Elamathi, V.; Varalakshmi, P.; Dhakshinamoorthy, A. Catal. Commun. 2020, 138, 105954.
[26]	Wilk, M.; Trzepizur, D.; Koszelewski, D.; Brodzka, A.; Ostasze- wski, R. Bioorg. Chem. 2019, 93, 102816.
[27]	Lolak, N.; Kuyuldar, E.; Burhan, H.; Goksu, H.; Akocak, S.; Sen, F. ACS Omega 2019, 4, 6848.
[28]	Yang, Y.; Wang, D.; Jiang, P. F.; Gao, W. L.; Cong, R. H.; Yang, T. Mol. Catal. 2020, 490, 110914.
[29]	Wang, W. F.; Luo, M.; Yao, W. W.; Ma, M. T.; Pullarkat, S. A.; Xu, L.; Leung, P.-H. Chem. Eng. 2019, 7, 1718.
[30]	Takakura, R.; Koyama, K.; Kuwata, M.; Yamada, T.; Sajiki, H.; Sawama, Y. Org. Biomol. Chem. 2020, 18, 6594. doi: 10.1039/d0ob01397h pmid: 32813006
[31]	Watson, G.; Derakhshandeh, P. G.; Abednatanzi, S.; Schmidt, J.; Leus, K.; Van der Voort, P. Molecules, 2021, 26, 838.
[32]	Abedian-Dehaghani, N.; Sadjadi, S.; Heravi, M. M. Sci. Rep. 2022, 12, 16395. doi: 10.1038/s41598-022-20699-2 pmid: 36180555
[33]	Sakata, N.; Sasakura, K.; Matsushita, G.; Okamoto, K.; Ohe, K. Org. Lett. 2017, 19, 3422. doi: 10.1021/acs.orglett.7b01378 pmid: 28657324
[34]	Zhang, Y.; Wei, Y.; Li, S.; Ma, J.-A. Eur. J. Org. Chem. 2019, 2019, 199. doi: 10.1002/ejoc.201801504
[35]	Li, Z.; Liu, C.; Wang, J.; Wang, S. J.; Xiao, L. W.; Jing, X. M. Spectrochim. Acta, Part A 2019, 212, 349.
[36]	Sarveswari, S.; Beneto, A. J.; Siva, A. Sens. Actuators, B 2017, 245, 428.
[37]	Cesaretti, A.; Foggi, P.; Fortuna, C. G.; Elisei, F.; Spalletti, A.; Carlotti, B. J. Phys. Chem. C 2020, 124, 15739.
[38]	Khalid, M.; Khan, M. U.; Shafiq, I.; Hussain, R.; Ali, A.; Imran, M.; Braga, A. A. C.; Rehman, M. F, U.; Akram, M. S. R. Soc. Open Sci. 2021, 8, 210570.
[39]	Lv, G. L.; Xu, Y. Z.; Yang, J. J.; Li, W. H.; Li, C. X.; Sun, A. Y. Analyst 2020, 145, 6579.
[40]	Arunkumar, A.; Shanavas, S.; Acevedo, R.; Anbarasan, P. M. Opt. Quantum Electron. 2020, 52, 164.
[41]	Gong, P. P.; An, L. L.; Tong, J. F.; Liu, X. P.; Liang, Z. Z.; Li, J. F. Nanomaterials 2022, 12, 3700.
[42]	Yahya, M.; Seferoglu, N.; Barsella, A.; Achelle, S.; Seferoglu, Z. Spectrochim. Acta, Part A 2021, 248, 119178.
[43]	Yu, H.; Fang, Y.; Wang, J.; Zhang, Q.; Chen, S. J.; Wang, K.-P.; Hu, Z.-Q. Anal. Bioanal. Chem. 2022, 414, 6779.
[44]	Wang, Z.-Y.; Cao, X.-Y.; Li, Z.-H.; Shen, Q. CN 117664934, 2023.
[45]	Battal, A.; Kassa, S. B.; Gultekin, N. A.; Tavasli, M.; Onganer, Y. Spectrochim. Acta, Part A 2023, 304, 123350.
[46]	Huang, J. J.; Zhou, Y. H.; Wang, W. X.; Zhu, J. M.; Li, X. C.; Fang, M.; Wu, Z. Y.; Zhu, W. J.; Li, C. Spectrochim. Acta, Part A 2023, 286, 122011.
[47]	Ramesh, S.; Kumaresan, S. Microchem. J. 2021, 169, 106584.
[48]	Popczyk, A.; Chereta, Y.; El-Ghayourya, A.; Sahraoui, B.; Mysliwiec, J. Dyes Pigm. 2020, 177, 108300.
[49]	Chen, Z.-H.; Yu, S.-W.; Xu, W.-J.; Li, M.-X.; Zeng, Y.; Deng, S.-W.; Lin, J.-Y.; Wang, Z.-Y. Organics, 2024, 5, 46.
[50]	Tu, L. P.; Liu, J.; Zhang, Z. C.; Qi, Q. R.; Yao, S.; Huang, W. C. Analyst 2021, 146, 2221.
[51]	Jia, Y.; Guan, W.-L.; Liu, J.; Hu, J.-P.; Shi, B. B.; Yao, H.; Zhang, Y.-M.; Wei, T.-B.; Lin, Q. Chin. Chem. Lett. 2023, 34, 108082.
[52]	Shan, X. F.; Wu, S. T.; Shen, L. Y.; Peng, S. L.; Xu, H.; Wang, Z.-Y.; Yang, X.-J.; Huang, Y.-L.; Feng, X.; Redshaw, C.; Zhang, Q.-L. Dyes Pigm. 2023, 219, 111609.
[53]	Wang, B.-W.; Jiang, K.; Li, J.-X.; Luo, S.-H.; Wang, Z.-Y.; Jiang, H.-F. Angew. Chem. Int. Ed. 2020, 59, 2338.
[54]	Chen, S.-H.; Chen, Z.-H.; Jiang, K.; Cao, X.-Y.; Chen, L.-Y.; Ouyang, J.; Wang, Z.-Y. Spectrochim. Acta, Part A 2023, 300, 122905.
[55]	Xue, J.; Tang, F.; Ding, A. X.; He, F.; Huang, J. Y.; Kong, L.; Yang, J. X. J. Lumin. 2022, 250, 119119.
[56]	Delgado-Montiel, T.; Baldenebro-López, J.; Soto-Rojo, R.; Glossman- Mitnik, D. Molecules 2020, 25, 3670.
[57]	Özarslan, A.; Çakmaz, D.; Erol, F.; Senöz, H.; Seferoglu, N.; Barsella, A.; Seferoglu, Z. J. Mol. Struct. 2021, 1229, 129583.
[58]	Mustafa, F. M.; Abdel-Latif, M. K.; Abdel-Khalek, A. A.; Kühn, O. Molecules, 2023, 28, 5185.
[59]	Han, L.; Chen, Q. Q.; Yu, H. D.; Lu, Y.; Jiang, S. L. J. Photochem. Photobiol. A 2021, 416, 113341.
[60]	Duvva, N.; Eom, Y. K.; Reddy, G.; Schanze, K. S.; Giribabu, L. ACS Appl. Energy Mater. 2020, 3, 6758.
[61]	Al-Marhabi, A. R.; El-Shishtawy, R. M.; Bouzzine, S. M.; Hamidi, M.; Al-Ghamdi, H. A.; Al-Footy, K. O. J. Photochem. Photobiol. A 2023, 436, 114389.
[62]	Xu, D. Q.; Tong, H. S.; Shen, J.; Qiu, W. W.; Qian, L. S. Chin. J. Org. Chem. 2024, 44, 1240 (in Chinese).
	(徐冬青, 童海姗, 沈杰, 邱万伟, 钱立生, 有机化学, 2024, 44, 1240.) doi: 10.6023/cjoc202309008
[63]	Kula, S.; Szlapa-Kula, A.; Fabianczyk, A.; Gnida, P.; Libera, M.; Bujak, K.; Siwy, M.; Schab-Balcerzak, E. J. Photochem. Photobiol. B 2019, 197, 111555.
[64]	Xu, C.-J.; Li, H.-W.; He, X.-L.; Du, W.; Chen, Y.-C. Asian J. Org. Chem. 2019, 8, 1037.
[65]	Manneveau, M.; Tanii, S.; Gens, F.; Legros, J.; Chataigner, I. Org. Biomol. Chem. 2020, 18, 3481. doi: 10.1039/d0ob00582g pmid: 32347286
[66]	Yuan, J. W.; Shen, L.; Guo, N.; Yin, Y. L.; Yang, P. Y.; Yang, L. R.; Xiao, Y. M.; Zhang, S. R. J. Org. Chem. 2023, 88, 16598.
[67]	Wang, N.; Yan, X.; Hu, Z.-T.; Feng, Y.; Zhu, L.; Chen, Z.-H.; Wang, H.; Wang, Q.-L.; Ouyang, Q.; Zheng, P.-F. Org. Lett. 2022, 24, 8553. doi: 10.1021/acs.orglett.2c03578 pmid: 36377976
[68]	Ben Hassen, M.; Masmoudi, F.; Zribi, L.; Trigui, M.; Ismaili, L.; Marco-Contelles, J.; Chabchoub, F. ChemistrySelect 2021, 6, 945. doi: 10.1002/slct.202004577
[69]	Hayashi, Y.; Kranidiotis-Hisatomi, N.; Sakamoto, D.; Oritani, K.; Kawamoto, T.; Kamimura, A. Eur. J. Org. Chem. 2019, 2018, 6843.
[70]	Hayashi, Y.; Odoh, A. S.; Kranidiotis-Hisatomi, N. ChemCatChem 2020, 12, 2412.
[71]	Li, F.; Wang, X.; Liu, Y. M.; Zhang, J.; Yang, J. Synth. Commun. 2020, 50, 56.
[72]	Zhang, W.; Tang, C.-S.; Xiang, S.-Q. RSC Adv. 2022, 12, 29840. doi: 10.1039/d2ra04936h pmid: 36321094
[73]	Lu, C. J.; Ye, M.; Long, L. P.; Zheng, Y.; Liu, J. M.; Zhang, Y.; Chen, Z. W. J. Org. Chem. 2022, 87, 1545.
[74]	Hu, L. J.; Lin, S. X.; Li, S. W.; Kang, Q.; Du, Y. ChemCatChem 2020, 12, 118.
[75]	Chen, X. J.; Zhao, Y. J.; Huang, C.; Zhao, Z. F.; Zhao, W. W.; Li, S.-W. Chem. Commun. 2024, 60, 236.
[76]	Bojanowski, J.; Albrecht, A. ChemistrySelect 2019, 4, 4588. doi: 10.1002/slct.201900579
[77]	Rout, S.; Ray, S. K.; Unhale, R. A.; Singh, V. K. Org. Lett. 2014, 16, 5568.
[78]	Martelli, L. S. R.; Vieira, L. C. C.; Paixao, M. W.; Zukerman- Schpector, J.; de Souza, J. O.; Aguiar, A. C. C.; Oliva, G.; Guido, R. V. C.; Corrêa, A. G. Tetrahedron 2019, 75, 3530. doi: 10.1016/j.tet.2019.05.022
[79]	Hayashi, Y.; Han, X. L.; Mori, N. Chem. Eur. J. 2023, 29, e202301093.
[80]	Wu, H.-C.; Wang, C.; Chen, Y.-H.; Liu, Y.-K. Chem. Commun. 2021, 57, 1762.
[81]	Wang, Y.; Niu, C.; Xie, D.-H.; Du, D.-M. Org. Biomol. Chem. 2021, 19, 8572. doi: 10.1039/d1ob01256h pmid: 34549755
[82]	Ittamalla, C.; Chintha, S.; Medishetti, N.; Nanubolu, J. B.; Atmakur, K. Eur. J. Org. Chem. 2023, 26, e202300357.
[83]	Cao, L.; Li, J.-X.; Wu, H.-Q.; Jiang, K.; Hao, Z.-F.; Luo, S.-H.; Wang, Z.-Y. ACS Sustainable Chem. Eng. 2018. 6, 4147.
[84]	Uchikura, T.; Toda, M.; Mouri, T.; Fujii, T.; Moriyama, K.; Ibáñez, I.; Akiyama, T. J. Org. Chem. 2020, 85, 12715.
[85]	Pálvölgyi, A. M.; Ehrschwendtner, F.; Schnürch, M.; Bica-Schröder, K. Org. Biomol. Chem. 2022, 20, 7245. doi: 10.1039/d2ob01364a pmid: 36073152
[86]	Yang, M.-L.; Dong, C.-L.; Guan, Z.; He, Y.-H. J. Org. Chem. 2024, 89, 1285.
[87]	Li, L.; Guo, S.; Wang, Q.; Zhu, J. Org. Lett. 2019, 21, 5462.
[88]	Matsumoto, A.; Yamamoto, M.; Maruoka, K. ACS Catal. 2022, 12, 2045.
[89]	Jia, Q. F.; Lan, Y. F.; Ye, X.; Lin, Y. H.; Ren, Q. RSC Adv. 2020, 10, 29171.
[90]	Liu, M.; Zhou, L. J.; Shi, W. Y.; Hu, Y. M.; Liao, J. N.; Duan, Z. Q.; Wang, W.; Wu, Y. J.; Zheng, B.; Guo, H. C. Org. Lett. 2021, 23, 7703.
[91]	Gao, Y.; Song, X.; Yan, R.-J.; Du, W.; Chen, Y.-C. Org. Biomol. Chem. 2021, 19, 151.
[92]	Zhang, J.; Xiong, D. K.; Jiang, Z. W.; Chen, S. T.; Huang, G.-B.; Li, J. S.; Wang, Z. M.; Yang, J. G. Org. Lett. 2024, 26, 1447. doi: 10.1021/acs.orglett.4c00078 pmid: 38353475
[93]	Yang, D. Z.; Zhu, M.; Wang, T. M.; He, Y. X.; Xie, L.; Zhang, J. Y.; Cheng, B. Org. Biomol. Chem. 2023, 21, 5413.
[94]	Yuan, C.; Tan, H.; Jiang, X.-F.; Liu, S.; Jiang, L.; Cao, Q.-Y.; Xu, X.-J.; Deng, X.-Y.; Pan, G.-N.; Chen, J.-Y.; Cui, H.-L. Asian J. Org. Chem. 2019, 8, 1893.
[95]	Dai, C. L.; Li, M. S.; Chen, M. J.; Luo, N. L.; Wang, C. D. J. Chem. Res. 2019, 43, 43.
[96]	Kowalska, E.; Dyguda, M.; Artelska, A.; Albrecht, A. J. Org. Chem. 2023, 88, 16589. doi: 10.1021/acs.joc.3c02172 pmid: 38037694
[97]	Radwan, M. F.; Elboray, E. E.; Dardeer, H. M.; Kobayashi, Y.; Furuta, T.; Hamada, S.; Dohi, T.; Aly, M. F. Chem. Asian J. 2023, 18, e202300215.
[98]	Zhou, Y.; Gao, C.-F.; Ma, H.; Nie, J.; Ma, J.-A.; Zhang, F.-G.; Zhang, Y. CCS Chem. 2022, 4, 3693.
[99]	Lukasik, B.; Romaniszyn, M.; Kloszewski, N.; Albrecht, L. Org. Lett. 2023, 25, 3728.
[100]	Romaniszyn, M.; Gronowska, K.; Albrecht, L. J. Org. Chem. 2019, 84, 9929. doi: 10.1021/acs.joc.9b01091 pmid: 31244164
[101]	Romaniszyn, M.; Sieron, L.; Albrecht, L. J. Org. Chem. 2022, 87, 5296.
[102]	Obydennov, D. L.; Simbirtseva, A. E.; Piksin, S. E.; Sosnovskikh, V. Y. ACS Omega 2020, 5, 33406. doi: 10.1021/acsomega.0c05357 pmid: 33403303
[103]	Xie, X. F.; Wang, L.; Zhou, Q.; Ma, Y. M.; Wang, Z.-M.; Li, P. H. Chin. Chem. Lett. 2022, 33, 5069.
[104]	Guo, M. Z.; Dong, F. Y.; Yin, X. C.; Xu, L. B.; Wang, L.; Li, S.-S. Org. Chem. Front. 2021, 8, 2224.
[105]	Wang, N.; Lin, J.-Y.; Luo, S.-H.; Zhou, Y.-J.; Yang, K.; Chen, R.-H.; Yang, G.-X.; Wang, Z.-Y. Amino Acids 2022, 54, 989.
[106]	Zhou, Y.-J.; Fang, Y.-G.; Yang, K.; Yu, S.-W.; Chen, Z.-J.; Wang, B.-C.; Zhan, H.-Y.; Wang, Z.-Y. Asian J. Org. Chem. 2023, 12, e202300038.
[107]	Zhou, Y.-J.; Fang, Y.-G.; Yang, K.; Lin, J.-Y.; Li, H.-Q.; Chen, Z.-J.; Wang, Z.-Y. Molecules 2023, 28, 5635.
[108]	Kornfeind, J.; Allen, James E.; Keller, Taylor M.; Fleming, Fraser F. J. Org. Chem. 2023, 88, 15947. doi: 10.1021/acs.joc.3c02210 pmid: 37938807
[109]	Liu, Q.-P.; Chen, X. Y.; Yu, N.; Li, Y.-L.; He, K.-C.; Zheng, W.-H.; Zhou, Y.-Q.; Jiang, K.; Yang, L. M.; Wei, Y. ACS Catal. 2023, 13, 5795.
[110]	Suzuki, I.; Kasahara, N.; Ogura, K.; Shibata, I. Chem.-Eur. J. 2024, 30, e202302365.
[111]	Suzuki, I.; Ogura, K.; Shimazu, J.; Shibata, I. Eur. J. Org. Chem. 2021, 2021, 2785.
[112]	Suzuki, I.; Tsunoi, S.; Shibata, I. Org. Lett. 2017, 19, 2690. doi: 10.1021/acs.orglett.7b01023 pmid: 28459596
[113]	Suzuki, I.; Shimazu, J. -Y.; Tsunoi, S.; Shibata, I. Eur. J. Org. Chem. 2019, 2019, 3658. doi: 10.1002/ejoc.201900518
[114]	Zhang, Y. J.; Shi, S. K.; Yang, Z. H. J. Org. Chem. 2024, 89, 2748.
[115]	Yang, Z. M.; Z, T. T.; Cao, B. Y.; Liao, D. J.; Hu, X. Y.; Zhao, S. L.; Qin, J. K. Mater. Today Chem. 2024, 35, 101890.
[116]	Xiao, F. F.; Lei, D.; Liu, C. G.; Li, Y. S.; Ren, W. F.; Li, J. G.; Li, D. Z.; Zu, B. Y.; Dou, X. C. Angew. Chem. Int. Ed. 2024, 63, e20240045.
[117]	Mwalukuku, V. M.; Liotier, J.; Riquelme, A. J.; Kervella, Y.; Huaul- me, Q.; Haurez, A.; Narbey, S.; Anta, J. A.; Demadrille, R. Adv. Energy Mater. 2023, 13, 2203651.
[118]	Chen, Z. H.; Zhang, S. Q.; Zhang, T.; Ren, J. Z.; Dai, J. B.; Li, H. X.; Qiao, J. W.; Hao, X. T.; Hou, J. H. Angew. Chem. Int. Ed. 2024, 63, e202317892.