Research Progress on Preparation and Application of Cyanoethylenes

doi:10.6023/cjoc20203013

Abstract

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

Cite this article

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.

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Fig. & Tab. 11

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

Scheme 2. Synthesis and detection mechanism of probe 5

Scheme 3. Synthesis and detection mechanism of probe 6

Scheme 4. Synthesis and detection mechanism of probe 7

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

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

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

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

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

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

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

References 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.

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