Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters

doi:10.6023/A23040118

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (6): 657-668.DOI: 10.6023/A23040118 Previous Articles Next Articles

Review

4-酰基/氨基羰基/烷氧羰基取代汉斯酯参与的有机反应研究进展

刘坜^a^,^b, 郑刚^a, 范国强^a, 杜洪光^b^,^*(), 谭嘉靖^b^,^*()

a 中石化(北京)化工研究院有限公司北京 100013
b 北京化工大学化学学院北京 100029

投稿日期:2023-04-06 发布日期:2023-05-11

作者简介:

刘坜, 工程师, 北京化工大学化学学院化学专业2018级博士研究生, 研究方向为绿色化学以及光化学有机合成, 累计发表SCI论文5篇. 现就职于中石化(北京)化工研究院有限公司, 研究方向为茂金属催化剂合成.

郑刚, 中石化(北京)化工研究院有限公司高级工程师, 硕士, 2013年获中石化科技进步一等奖(排名第三), 2020年获中石化前瞻性基础性研究二等奖(排名第三). 从事单中心催化剂开发应用研究, 在茂金属催化剂的工业应用、产品开发等领域取得系列进展, 获得中国专利授权70余项.

范国强, 中石化(北京)化工研究院有限公司高级工程师, 博士, 主要从事茂金属催化剂及聚烯烃的研究开发工作, 研究开发了聚丙烯、聚乙烯及聚烯烃弹性体等系列茂金属催化剂, 开发的聚丙烯茂金属催化剂已成功工业应用. 2011年获中国石化科技进步奖一等奖, 2020年获中国石化前瞻性基础性研究科学奖二等奖.

杜洪光, 博士, 北京化工大学化学学院教授, 博士生导师. 主要研究领域为药物化学和有机合成方法学, 累计发表SCI论文70余篇.

谭嘉靖, 博士, 副教授. 本科毕业于中国科学技术大学, 2013年于美国芝加哥大学化学系获得博士学位, 师从Hisashi Yamamoto教授. 2013年至2016年在美国默沙东公司工艺化学部担任副研究员, 从事手性药物合成工艺研究. 2016年受聘到北京化工大学理学院(现化学学院), 担任副教授. 课题组长期在有机合成方法学和药物化学领域从事研究, 累计发表SCI论文50余篇. 作为项目负责人先后承担国家自然科学基金(面上、青年)、北京市自然科学基金. 作为项目骨干参与国家重点研发计划子课题.

基金资助:
国家自然科学基金(21702013); 国家自然科学基金(22271010); 北京化工大学中央高校基本科研业务费专项资金(XK1802-6)

Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters

Li Liu^a^,^b, Gang Zheng^a, Guoqiang Fan^a, Hongguang Du^b(), Jiajing Tan^b()

a Sinopec Beijing Research Institute of Chemical Industry, Beijing 100013
b Beijing University of Chemical Technology, College of Chemistry, Beijing 100029

Received:2023-04-06 Published:2023-05-11
Contact: *E-mail: dhg@mail.buct.edu.cn; tanjj@mail.buct.edu.cn
Supported by:
National Natural Science Foundation of China(21702013); National Natural Science Foundation of China(22271010); Fundamental Research Funds for the Central Universities in BUCT(XK1802-6)

In recent years, 4-acyl/carbamoyl/alkoxycarbonyl-substituted Hantzsch esters have been increasingly utilized as a new class of radical precursor reagents, emerging as one of major research topics for synthetic chemists. These compounds can generate the corresponding acyl, carbamoyl, and alkoxycarbonyl radicals under mild conditions through photochemical, electrochemical, or chemical oxidation systems, leading to a wide array of radical addition/coupling reactions. Due to the reducibility of their dihydropyridine skeleton, these radical precursors often exhibit unique reactivities and display good compatibility with transition metal-catalysis and organocatalysis systems. In addition, the reported reaction conditions typically feature for environmental friendliness, highly functional group-tolerance, and biocompatibility, which should have significant research value in the fields of medicinal chemistry and chemical biology. Herein, this review summarizes the research progress of acyl, carbamoyl and alkoxycarbonyl radicals, and focuses on radical generation system, mechanistic underpinnings, as well as the uniqueness and applications of the synthetic strategies with such Hantzsch esters.

Key words: 4-substituted Hantzsch esters, acyl/carbamoyl/alkoxycarbonyl radicals, photocatalysis, electro-organic synthesis, green chemistry

Cite this article

Li Liu, Gang Zheng, Guoqiang Fan, Hongguang Du, Jiajing Tan. Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters[J]. Acta Chimica Sinica, 2023, 81(6): 657-668.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 19

Figure 1. DHP catalogue and mechanism of acyl radical generation from 4-acyl substituted Hantzsch esters

Figure 2. Stereoselective synthesis of 1,4-dicarbonyl compounds

Figure 3. Photochemical C—H hydroxyalkylation of quinolines and isoquinolines

Figure 4. Co-catalyzed visible-light-induced enantioselective radical conjugate addition

Figure 5. Visible-light-promoted hydroacylation and diacylation of alkenes

Figure 6. Photochemical acylation of 2H-indazoles and benzothiazoles

Figure 7. Access to deuterated α-amino acids and peptides by photochemical acyl radical addition

Figure 8. Acylation of benzoxazinones with acyl substituted Hantzsch esters

Figure 9. Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles

Figure 10. Photocatalyst-free hydroacylations of electron-deficient alkenes and enones under visible-light irradiation

Figure 11. Functionalization of pyridinium derivatives enabled by photoinduced charge transfer

Figure 12. Decarbonylative trifluoromethylthiolation of substituted Hantzsch ester enabled by EDA complex photoactivation

Figure 13. The conversion of 4-substituted Hantzsch esters into ynones under electrochemical conditions

Figure 14. Amide synthesis by nickel/photoredox-catalyzed direct carbamoylation of (hetero)aryl bromides

Figure 15. Photoredox-catalyzed addition of carbamoyl radicals to olefins

Figure 16. Photoredox-catalyzed synthesis of α-amino acid amides by imine carbamoylation

Figure 17. Carbamoylation of azomethine imines via visible-light photoredox catalysis

Figure 18. Site-selective itaconation of complex peptides by photoredox catalysis

Figure 19. Reactions of alkoxycarbonyl substituted Hantzsch esters

References 38

[1]	Hantzsch, A. Ber. Dtsch. Chem. Ges. 1881, 14, 1637. doi: 10.1002/cber.v14:2
[2]	(a) Li, G. X.; Chen, R.; Wu, L.; Fu, Q. Q.; Zhang, X. M.; Tang, Z. Angew. Chem., Int. Ed. 2013, 52, 8432. doi: 10.1002/anie.v52.32
	(b) Li, G. X.; Wu, L.; Lv, G.; Li, H. X.; Fu, Q. Q.; Zhang, X. M.; Tang, Z. Chem. Commun. 2014, 50, 6246. doi: 10.1039/C4CC01119H
[3]	(a) Wang, P.-Z.; Chen, J.-R.; Xiao, W.-J. Org. Biomol. Chem. 2019, 17, 6936. doi: 10.1039/C9OB01289C
	(b) Ye, S. Q.; Wu, J. Acta Chim. Sinica 2019, 77, 814. (in Chinese) doi: 10.6023/A19050170
	(叶盛青, 吴劼, 化学学报, 2019, 77, 814.) doi: 10.6023/A19050170
	(c) Chen, Y. F.; Zhao, H.; Cheng, D. P.; Li, X. N.; Xu, X. L. Chin. J. Org. Chem. 2020, 40, 1297. (in Chinese) doi: 10.6023/cjoc201911024
	(陈跃峰, 赵赫, 程冬萍, 李小年, 许孝良, 有机化学, 2020, 40, 1297.) doi: 10.6023/cjoc201911024
	(d) Li, T. T.; Cheng, X. K.; Lu, J. M.; Wang, H. F.; Fang, Q.; Lu, Z. Chin. J. Chem. 2022, 40, 1033. doi: 10.1002/cjoc.v40.9
	(e) Huang, W. H.; Cheng, X. Synlett 2017, 28, 148. doi: 10.1055/s-0036-1588129
[4]	Nakajima, K.; Nojima, S.; Sakata, K.; Nishibayashi, Y. ChemCatChem 2016, 8, 1028. doi: 10.1002/cctc.v8.6
[5]	Chen, W. X.; Liu, Z.; Tian, J. Q.; Li, J.; Ma, J.; Cheng, X.; Li, G. G. J. Am. Chem. Soc. 2016, 138, 12312. doi: 10.1021/jacs.6b06379
[6]	(a) Phelan, J. P.; Lang, S. B.; Sim, J.; Berritt, S.; Peat, A. J.; Billings, K.; Fan, L.; Molander, G. A. J. Am. Chem. Soc. 2019, 141, 3723. doi: 10.1021/jacs.9b00669 pmid: 27990318
	(b) Buzzetti, L.; Prieto, A.; Roy, S. R.; Melchiorre, P. Angew. Chem., Int. Ed. 2017, 56, 15039. doi: 10.1002/anie.201709571 pmid: 27990318
	(c) Nakajima, K.; Nojima, S.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2016, 55, 14106. doi: 10.1002/anie.201606513 pmid: 27990318
	(d) Gutiérrez-Bonet, Á.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004. pmid: 27990318
[7]	(a) van Leeuwen, T.; Buzzetti, L.; Perego, L. A.; Melchiorre, P. Angew. Chem., Int. Ed. 2019, 58, 4953. doi: 10.1002/anie.201814497 pmid: 30747467
	(b) Verrier, C.; Alandini, N.; Pezzetta, C.; Moliterno, M.; Buzzetti, L.; Hepburn, H. B.; Vega- Peñaloza, A.; Silvi, M.; Melchiorre, P. ACS Catal. 2018, 8, 1062. doi: 10.1021/acscatal.7b03788 pmid: 30747467
[8]	Wu, Q.-Y.; Min, Q.-Q.; Ao, G.-Z.; Liu, F. Org. Biomol. Chem. 2018, 16, 6391. doi: 10.1039/C8OB01641K
[9]	Gu, F. J.; Huang, W. H.; Liu, X.; Chen, W. X.; Cheng, X. Adv. Synth. Catal. 2018, 360, 925. doi: 10.1002/adsc.v360.5
[10]	de Assis, F. F.; Huang, X. Q.; Akiyama, M.; Pilli, R. A.; Meggers, E. J. Org. Chem. 2018, 83, 10922. doi: 10.1021/acs.joc.8b01588
[11]	Goti, G.; Bieszczad, B.; Vega-Peñaloza, A.; Melchiorre, P. Angew. Chem. Int. Ed. 2019, 58, 1213. doi: 10.1002/anie.v58.4
[12]	(a) Loh, Y. Y.; Nagao, K.; Hoover, A. J.; Hesk, D.; Rivera, N. R.; Colletti, S. L.; Davies, I. W.; MacMillan, D. W. C. Science 2017, 358, 1182. doi: 10.1126/science.aap9674 pmid: 28762417
	(b) Gan, Z.-Y.; Li, G.-Q.; Yang, X.-B.; Yan, Q.-L.; Xu, G.-Y.; Li, G.-Y.; Jiang, Y.-Y.; Yang, D.-S. Sci. China: Chem. 2020, 63, 1652. doi: 10.1007/s11426-020-9811-6 pmid: 28762417
	(c) Xie, J.; Jin, H. M.; Hashmi, A. S. K. Chem. Soc. Rev. 2017, 46, 5193. doi: 10.1039/c7cs00339k pmid: 28762417
	(d) Wu, X. T.; Zhao, F.; Ji, X. Z.; Huang, H. W. Chin. J. Org. Chem. 2022, 42, 4323. (in Chinese) doi: 10.6023/cjoc202208036 pmid: 28762417
	(巫晓婷, 赵峰, 姬小趁, 黄华文, 有机化学, 2022, 42, 4323.) doi: 10.6023/cjoc202208036 pmid: 28762417
	(e) Zhang, J.; Chen, Y. Y. Acta Chim. Sinica 2017, 75, 41. doi: 10.6023/A16080416 pmid: 28762417
	(张晶, 陈以昀, 化学学报, 2017, 75, 41.) doi: 10.6023/A16080416 pmid: 28762417
	(f) Gao, P. P.; Xiao, W. J.; Chen, J. R. Chin. J. Org. Chem. 2022, 42, 3923. (in Chinese) doi: 10.6023/cjoc202208044 pmid: 28762417
	(高盼盼, 肖文精, 陈加荣, 有机化学, 2022, 42, 3923.) doi: 10.6023/cjoc202208044 pmid: 28762417
[13]	Bieszczad, B.; Perego, L. A.; Melchiorre, P. Angew. Chem. Int. Ed. 2019, 58, 16878. doi: 10.1002/anie.201910641 pmid: 31529788
[14]	Buzzetti, L.; Crisenza, G. E. M.; Melchiorre, P. Angew. Chem., Int. Ed. 2019, 58, 3730. doi: 10.1002/anie.201809984 pmid: 30339746
[15]	Zhang, K.; Lu, L.-Q.; Jia, Y.; Wang, Y.; Lu, F.-D.; Pan, F. F.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 13375. doi: 10.1002/anie.201907478 pmid: 31293048
[16]	Zhao, X. X.; Li, B.; Xia, W. J. Org. Lett. 2020, 22, 1056. doi: 10.1021/acs.orglett.9b04595
[17]	Liu, L.; Jiang, P. X.; Liu, Y. G.; Du, H. G.; Tan, J. J. Org. Chem. Front. 2020, 7, 2278. doi: 10.1039/D0QO00507J
[18]	Jiang, P. X.; Liu, L.; Tan, J. J.; Du, H. G. Org. Biomol. Chem. 2021, 19, 4487. doi: 10.1039/D1OB00734C
[19]	(a) Lau, J. L.; Dunn, M. K. Bioorg. Med. Chem. 2018, 26, 2700. doi: 10.1016/j.bmc.2017.06.052
	(b) Guo, Y. F.; Zhuang, Z.; Liu, Y. G.; Yang, X.; Tan, C.; Zhao, X. W.; Tan, J. J. Coord. Chem. Rev. 2022, 463, 214525.
[20]	Liu, L.; Deng, Z. K.; Xu, K.; Jiang, P. X.; Du, H. G.; Tan, J. J. Org. Lett. 2021, 23, 5299. doi: 10.1021/acs.orglett.1c01448
[21]	Byun, Y.; Moon, J.; An, W.; Mishra, N. K.; Kim, H. S.; Ghosh, P.; Kim, I. S. J. Org. Chem. 2021, 86, 12247. doi: 10.1021/acs.joc.1c01558
[22]	Zeng, F.-L.; Xie, K.-C.; Liu, Y.-T.; Wang, H.; Yin, P.-C.; Qu, L.-B.; Chen, X.-L.; Yu, B. Green Chem. 2022, 24, 1732. doi: 10.1039/D1GC04218A
[23]	Pálvölgyi, Á. M.; Ehrschwendtner, F.; Schnürch, M.; Bica-Schröder, K. Org. Biomol. Chem. 2022, 20, 7245. doi: 10.1039/d2ob01364a pmid: 36073152
[24]	(a) Crisenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461. doi: 10.1021/jacs.0c01416 pmid: 32134647
	(b) Hota, S, K.; Panda, S. P.; Das, S.; Mahapatra, S. K.; Roy, L.; Sarkar, S. D.; Murarka, S. J. Org. Chem. 2023, 88, 2543. doi: 10.1021/acs.joc.2c03044 pmid: 32134647
	(c) Choi, W.; Kim, M.; Lee, K.; Park, S.; Hong, S. Org. Lett. 2022, 24, 9452. doi: 10.1021/acs.orglett.2c03882 pmid: 32134647
[25]	Kim, I.; Park, S.; Hong, S. Org. Lett. 2020, 22, 8730. doi: 10.1021/acs.orglett.0c03347
[26]	Lipp, A.; Badir, S. O.; Dykstra, R.; Gutierrez, O.; Molander, G. A. Adv. Synth. Catal. 2021, 363, 3507. doi: 10.1002/adsc.v363.14
[27]	(a) Fan, R.; Tan, C.; Liu, Y. G.; Wei, Y.; Zhao, X. W.; Liu, X. Y.; Tan, J. J.; Yoshida, H. Chin. Chem. Lett. 2021, 32, 299. doi: 10.1016/j.cclet.2020.06.003
	(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. doi: 10.1039/B610213C
	(c) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432. doi: 10.1021/cr4002879
[28]	(a) Wang, H. Q.; Xu, K. Chin. J. Org. Chem. 2022, 42, 1260. (in Chinese) doi: 10.6023/cjoc202200021
	(王会巧, 徐坤, 有机化学, 2022, 42, 1260.) doi: 10.6023/cjoc202200021
	(b) Wang, H. Q.; Xu, K. Chin. J. Org. Chem. 2023, 43, 789. (in Chinese) doi: 10.6023/cjoc202300010
	(王会巧, 徐坤, 有机化学, 2023, 43, 789.) doi: 10.6023/cjoc202300010
[29]	Luo, X. S.; Wang, P. Org. Lett. 2021, 23, 4960. doi: 10.1021/acs.orglett.1c01243
[30]	(a) Greenberg, A.; Breneman, C. M.; Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science, Wiley-VCH, Weinheim, 2003. pmid: 26571338
	(b) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451. doi: 10.1021/jm200187y pmid: 26571338
	(c) Brown, D. G.; Bostrçm, J. J. Med. Chem. 2016, 59, 4443. doi: 10.1021/acs.jmedchem.5b01409 pmid: 26571338
[31]	Alandini, N.; Buzzetti, L.; Favi, G.; Schulte, T.; Candish, L.; Collins, K. D.; Melchiorre, P. Angew. Chem., Int. Ed. 2020, 59, 5248. doi: 10.1002/anie.v59.13
[32]	Cardinale, L.; Konev, M. O.; von Wangelin, A. J. Chem.-Eur. J. 2020, 26, 8239. doi: 10.1002/chem.202002410 pmid: 32428293
[33]	Cardinale, L.; Schmotz, M. W. S.; Konev, M. O.; von Wangelin, A. J. Org. Lett. 2022, 24, 506. doi: 10.1021/acs.orglett.1c03908
[34]	Matsuo, B. T.; Oliveira, P. H. R.; Correia, J. T. M.; Paixão, M. W. Org. Lett. 2021, 23, 6775. doi: 10.1021/acs.orglett.1c02353
[35]	(a) Henninot, A.; Collins, J. C.; Nuss, J. M. J. Med. Chem. 2018, 61, 1382. doi: 10.1021/acs.jmedchem.7b00318 pmid: 22917241
	(b) Albericio, F.; Kruger, H. G. Future Med. Chem. 2012, 4, 1527. doi: 10.4155/fmc.12.94 pmid: 22917241
	(c) Peng, X.; Xu, K.; Zhang, Q.; Liu, L.; Tan, J. J. Trends in Chemistry 2022, 4, 643. doi: 10.1016/j.trechm.2022.04.008 pmid: 22917241
[36]	Wang, S. Y.; Zhou, Q. Q.; Zhang, X. H.; Wang, P. Angew. Chem., Int. Ed. 2022, 61, e202111388.
[37]	Wei, Y. L.; Ben-zvi, B.; Diao, T. N. Angew. Chem. Int. Ed. 2021, 60, 9433. doi: 10.1002/anie.v60.17
[38]	Wei, Y. L.; Lam, J.; Diao, T. N. Chem. Sci. 2021, 12, 11414. doi: 10.1039/D1SC03596G

4-酰基/氨基羰基/烷氧羰基取代汉斯酯参与的有机反应研究进展

Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 19

References 38

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines [J]. Acta Chimica Sinica, 2024, 82(2): 190-212.
[2]	Yuhan Wu, Dongdong Zhang, Hongyu Yin, Zhengnan Chen, Wen Zhao, Yuhua Chi. Density Functional Theory Study of Janus In₂S₂X Photocatalytic Reduction of CO₂ under “Double Carbon” Target [J]. Acta Chimica Sinica, 2023, 81(9): 1148-1156.
[3]	Minghui He, Ziqiu Ye, Guiqing Lin, Sheng Yin, Xinyi Huang, Xu Zhou, Ying Yin, Bo Gui, Cheng Wang. Research Progress of Porphyrin-Based Covalent Organic Frameworks in Photocatalysis^★ [J]. Acta Chimica Sinica, 2023, 81(7): 784-792.
[4]	Jiawen Liu, Weihuang Lin, Weijia Wang, Xueyi Guo, Ying Yang. Synthesis and Photocatalytic Degradation of Cu_1.94S-SnS Nano-heterojunction [J]. Acta Chimica Sinica, 2023, 81(7): 725-734.
[5]	Fei Li, Huili Ding, Chaozhong Li. Hydrotrifluoromethylation of Alkenes with a Fluoroform-Derived Trifluoromethylboron Complex [J]. Acta Chimica Sinica, 2023, 81(6): 577-581.
[6]	Qi Xueping, Wang Fei, Zhang Jian. A Post-Synthetic Method for the Construction of Titanium-Based Metal Organic Frameworks and Their Applications [J]. Acta Chimica Sinica, 2023, 81(5): 548-558.
[7]	Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Radical-Based Dehydroxylation of Hydroxyl Groups via Oxalates [J]. Acta Chimica Sinica, 2023, 81(11): 1609-1623.
[8]	Chunhui Yang, Jingchao Chen, Xinhan Li, Li Meng, Kaimin Wang, Weiqing Sun, Baomin Fan. Difluoroallylation of Silanes under Photoirradiation [J]. Acta Chimica Sinica, 2023, 81(1): 1-5.
[9]	Zhongshu Xie, Zhongxin Xue, Ziwen Xu, Qian Li, Hongyu Wang, Wei-Shi Li. Conjugated Crosslinking Modification of Graphitic Carbon Nitrides and Its Effect on Visible Light-Driven Photocatalytic Hydrogen Production [J]. Acta Chimica Sinica, 2022, 80(9): 1231-1237.
[10]	Yu Qi, Fuxiang Zhang. Photocatalytic Water Splitting for Hydrogen Production^※ [J]. Acta Chimica Sinica, 2022, 80(6): 827-838.
[11]	Heng Shu, Yide-Rigen Bao, Yong Na. Photocatalytic Oxidation of 5-Hydroxymethylfurfural Selectively into 2,5-Diformylfuran with CdS Nanotube [J]. Acta Chimica Sinica, 2022, 80(5): 607-613.
[12]	Xue Gong, Xinguo Ma, Fengda Wan, Wangyang Duan, Xiaoling Yang, Jinrong Zhu. Study on the Electronic Structure and Optical Properties of Two-dimensional Monolayer MoSi₂X₄ (X=N, P, As) [J]. Acta Chimica Sinica, 2022, 80(4): 510-516.
[13]	Pan An, Qinghui Zhang, Zhuang Yang, Jiaxing Wu, Jiaying Zhang, Yajun Wang, Yuming Li, Guiyuan Jiang. Research Progress of Solar Hydrogen Production Technology under Double Carbon Target [J]. Acta Chimica Sinica, 2022, 80(12): 1629-1642.
[14]	Jingpeng Li, Qi Yang, Zhou Zhang, Guiyun Zeng, Teng Liu, Chao Huang. Highly Selective Synthesis of (Z)-N-vinyl Ring N,O-Acetal Derivatives by Multi-component Continuous Flow [J]. Acta Chimica Sinica, 2022, 80(11): 1463-1468.
[15]	Xiaohan Yu, Wei Huang, Yanguang Li. Controllable Synthesis and Photocatalytic Applications of Two-dimensional Covalent Organic Frameworks [J]. Acta Chimica Sinica, 2022, 80(11): 1494-1506.