Advances in Three-Component Coupling Reactions Involving CO2

doi:10.6023/cjoc202309013

Abstract

Carbon dioxide (CO₂) is the attractive green and renewable C1 resource, and its direct participation in organic synthesis reactions as a reaction feedstock or promoter, which is a research direction advocated by green chemistry. On the other hand, the three-component coupling reaction is considered to be one of the most attractive strategies in synthetic chemistry, which is capable of synthesizing complex molecules directly from simple and readily available raw materials. Based on this, this paper reviews the three-component coupling reaction systems involving CO₂ as a raw material or promoter, categorizes them according to the types of products generated: carboxyl, ester, carbonyl, haloalkyl, and cyano compounds as well as CO₂ as a promoter. An outlook on the development of such reactions is also given.

Key words: carbon dioxide, green chemistry, three-component coupling, promoter

Cite this article

Kun Xia, Kaifa Zhang, Sher Wali Khan, Abdukader Ablimit. Advances in Three-Component Coupling Reactions Involving CO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1506-1525.

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Fig. & Tab. 30

Figure 1. Heterocyclic compounds from new cyclization reactions using CO2

Scheme 1. Synthesis of higher carboxylic acids from ethers with CO2 and H2

Scheme 2. Synthesis of higher carboxylic acids from ketone or aldehyde with CO2 and H2

Scheme 3. Electrochemical β-selective hydrocarboxylation of styrene using CO2 and water

Scheme 4. Photocatalytic dicarboxylation of olefins with CO2 and formates

Scheme 5. Visible light-driven iron-promoted thiocarboxylation of olefins with CO2

Scheme 6. Aminocarboxylation of visible light-driven olefins with CO2

Scheme 7. Visible photooxidation-catalyzed remote difunctionalized carboxylation of unactivated olefins with CO2

Scheme 8. Arylmagnesium reagent, reaction of CO2 with alkynes to form trisubstituted acrylic acid

Scheme 9. Synthesis of carbamate from CO2 in DES solvent

Scheme 10. Electrocatalytic immobilization of CO2 by imines and aryl ketones

Scheme 11. Nickel and photocatalytic CO2 synthesis of aryl carbamates

Scheme 12. Direct C(sp2)—H bond esterification of diazo couples with CO2

Scheme 13. Photocatalytic coupling of ethynylbenziodoxolones, CO2 and amines

Scheme 14. Visible light driven reactive alkyl bromine and CO2 catalyzed oxygen alkylation of aniline

Scheme 15. [2＋2＋2] cyclization of aromatic hydrocarbons and CO2

Scheme 16. CO2 conversion through synergistic redox activation

Scheme 17. Three component reaction between CO2 and pyridine derivatives

Scheme 18. Palladium catalyzed formation of ketone heterocycles from CO2 and isocyanides

Scheme 19. Synthesis of thiazolidine amine from CO2, aromatic amine, and sulfur

Scheme 20. Synthesis of asymmetric urea with CO2 catalyzed by vanadium

Scheme 21. Reducing CO2 to methylene and regenerating it into disulfide acetal compounds

Scheme 22. N-Methylation reaction of CO2 with aniline under mild conditions

Scheme 23. N-heterocyclic imines as nucleophilic reagents catalyze the coupling reaction of amines with CO2

Scheme 24. BICAAC catalyzed CO2 participation in N-methylation of amides

Figure 25. One pot N-methylation cyclization reaction of CO2 with aromatic amines and ketene

Scheme 26. Selective cyanidation of aryl halides involving CO2 and NH3

Scheme 27. Selective cyanidation of aryl halides involving CO2 and NH3

Scheme 28. Three component streak reaction promoted by CO2

Scheme 29. Boronization of non active aromatic amines catalyzed by light and CO2

References 59

[1]	Ngo, L. H.; Mishra, K. M.; Mishra, V.; Chien, T. C. Chem. Eng. Sci. 2021, 229, 116142.
	Ran, C. K.; Liao, L. L.; Gao, T. Y.; Gui, Y. Y.; Yu, D. G. Curr. Opin. Green Sustainable Chem. 2021, 32, 100525.
[2]	Guo, Y. H.; Li, W.; Wen, Z. L.; Qi, C. R.; Jiang, H. F. Acta Phys. Chim. Sin. 2023, 40, 2307004 (in Chinese).
	( 郭艳辉, 魏丽, 温中林, 戚朝荣, 江焕峰, 物理化学学报, 2023, 40, 2307004.)
[3]	Huang, W.; Lin, J. Y.; Deng, F.; Zhong, H. Asian J. Org. Chem. 2022, 11, e202200220.
[4]	Mao, B.; Wei, J. S.; Shi, M. Chem. Commun. 2022, 58, 9312.
[5]	Ye, J. H.; Ju, T.; Huang, H.; Liao, L. L.; Yu, D. G. Acc. Chem. Res. 2021, 54, 2518.
[6]	Zhang, Z.; Gong, L.; Zhou, X. Y.; Yan, S. S.; Li, J.; Yu, D. G. Acta Chim. Sinica 2019, 77, 783 (in Chinese). doi: 10.6023/A19060208
	( 张振, 龚莉, 周晓渝, 颜思顺, 李静, 余达刚, 化学学报, 2019, 77, 783.) doi: 10.6023/A19060208
[7]	Zhang, Z.; Ye, J. H.; Ju, T.; Liao, L. L.; Huang, H.; Gui, Y. Y.; Yu, D. G. ACS Catal. 2020, 10, 10871.
[8]	Liao, L. L.; Wang, Z. H.; Cao, K. G.; Sun, G. Q.; Zhang, W.; Ran, C. K.; Yu, D. G. J. Am. Chem. Soc. 2022, 144, 2062.
[9]	Seo, H.; Nguyen, L. V.; Jamison, T. F. Adv. Synth. Catal. 2019, 361, 247.
[10]	Zhou, Z. H.; Xia, S. M.; He, L. N. Acta Phys., Chim. Sin. 2018, 34, 838 (in Chinese).
	( 周智华, 夏书梅, 何良年, 物理化学学报, 2018, 34, 838.)
[11]	Qiu, L. Q.; Li, H. R.; He, L. N. Acc. Chem. Res. 2023, 56, 2225.
[12]	Saranya, S.; Rohit, K.; Radhika, S.; Anilkumar, G. Org. Biomol. Chem. 2019, 17, 8048. doi: 10.1039/c9ob01538h pmid: 31410440
[13]	Mannich, C.; Krösche, W. Arch. Pharm. 1912, 250, 647.
[14]	Strecker, A. Justus Liebigs Ann. Chem. 1854, 91, 349.
[15]	Ugi, I.; Meyr, R.; Fetzer, U.; Steinbruckner, C. Angew. Chem. 1959, 71, 386.
[16]	Wu, P.; Givskov, M.; Nielsen, T. E. Chem. Rev. 2019, 119, 11245. doi: 10.1021/acs.chemrev.9b00214
[17]	Tian, Y. M.; Wang, H.; König, B. Chem. Sci. 2022, 13, 241.
[18]	Okumura, S.; Takahashi, T.; Torii, K.; Uozumi, Y. Chem.-Eur. J. 2023, e202300840.
[19]	Chatterjee, R.; Bhaumik, A. Curr. Org. Chem. 2022, 26, 60.
[20]	Sang, R.; Kucmierczyk, P.; Dühren, R.; Razzaq, R.; Dong, K. W.; Liu, J.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2019, 58, 14365. doi: 10.1002/anie.201908451 pmid: 31390131
[21]	Wang, Y.; Qian Q. L; Zhang, J. J.; Bediako, B. A.; Wang, Z. P.; Liu, H. Z.; Han, B. X. Nat. Commun. 2019, 10, 5395.
[22]	Zhang, Y.; Zhang, J.; Wang, Y.; Li, Y.; He, J.; Wang, Y.; Han, B. X. Organometallics 2023, 42, 2312.
[23]	Kim, Y.; Park, G. D.; Balamurugan, M.; Seo, J.; Min, B. K.; Nam, K. T. Adv. Sci. 2020, 7, 1900137.
[24]	Xu, P.; Wang, S.; Xu, H.; Liu, Y. Q.; Li, R. B.; Liu, W. W.; Zhu, X. ACS Catal. 2023, 13, 2149.
[25]	Ye, J. H.; Miao, M.; Huang, H.; Yan, S. S.; Yin, Z. B.; Zhou, W. J.; Yu, D. G. Angew. Chem., Int. Ed. 2017, 56, 15416.
[26]	Yue, J. P.; Xu, J. C.; Luo, H. T.; Chen, X. W.; Song, H. X.; Deng, Y.; Yu, D. G. Nat. Catal. 2023, 6, 959.
[27]	Song, L.; Fu, D. M.; Chen, L.; Jiang, Y. X.; Ye, J. H.; Zhu, L.; Lan, Y.; Fu, Q.; Yu, D. G. Angew. Chem., nt. Ed. 2020, 59, 21121.
[28]	Zhang, W. Z.; Zhang, N.; Guo, X. C.; Lü, X. B. Chin. J. Org. Chem. 2017, 37, 1309 (in Chinese).
	( 张文珍, 张宁, 郭春晓, 吕小兵, 有机化学, 2017, 37, 1309.)
[29]	Wang, S.; Xi, C. J. Org. Lett. 2018, 20, 4131.
[30]	Deng, Y. Q.; Yang, T. B.; Wang, H.; Yang, C.; Cheng, L. H.; Yin, S. F.; Kambe, N.; Qiu, R. H. Top. Curr. Chem. 2021, 379, 42.
[31]	Sun, L.; Ye, J. H.; Zhou, W. J.; Zeng, X.; Yu, D. G. Org. Lett. 2018, 20, 3049.
[32]	Inaloo, I. D.; Majnooni, S. New J. Chem. 2019, 43, 11275.
[33]	Wang, J. W.; Qian, P.; Hu, K. F.; Zha, Z. G.; Wang, Z. Y. ChemElectroChem 2019, 6, 4292.
[34]	Sahari, A.; Puumi, J.; Mannisto, J. K.; Repo, T. J. Org. Chem. 2023, 88, 3822.
[35]	Liu, Q. Y.; Li, M.; Xiong, R.; Mo, F. Y. Org. Lett. 2017, 19, 6756.
[36]	Wang, L.; Shi, F. X.; Qi, C. R.; Xu, W. J.; Xiong, W. F.; Kang, B. X.; Jiang, H. F. Chem. Sci. 2021, 12, 11821. doi: 10.1039/d1sc03366b pmid: 34659721
[37]	Sun, S.; Zhou, C.; Yu, J. T.; Cheng, J. Org. Lett. 2019, 21, 6579.
[38]	Liu, S. Q.; Zhang, K.; Meng, Y. T.; Xu, J. X.; Chen, N. Org. Biomol. Chem. 2023, 21, 6892.
[39]	Zhang, S. K.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2020, 49, 3187.
[40]	Mancuso, R. Catalysts 2021, 11, 470.
[41]	Lian, Z.; Nielsen, D. U.; Lindhardt, A. T.; Daasbjerg, K.; Skryd- strup, T. Nat. Commun. 2016, 7, 13782.
[42]	Cerveri, A.; Pace, S.; Monari, M.; Lombardo, M.; Bandini, M. Chem.-Eur. J. 2019, 25, 15272.
[43]	Mampuys, P.; Neumann, H.; Sergeyev, S.; Orru, R. V. A.; Jiao, H.; Spannenberg, A.; Maes, B. U. W.; Beller, M. ACS Catal. 2017, 7, 5549.
[44]	Ran, C. K.; Song, L.; Niu, Y. N.; Wei, M. K.; Zhang, Z.; Zhou, X. Y.; Yu, D. G. Green Chem. 2021, 23, 274.
[45]	Matsutani, T.; Aoyama, K.; Moriuchi, T. Organometallics 2023, 42, 1310.
[46]	Moulay, S. Curr. Org. Chem. 2018, 22, 1986.
[47]	Zhang, X. W.; Wang, S.; Xi, C. J. J. Org. Chem. 2019, 84, 9744.
[48]	Guo, Z. Q.; Zhang, B.; Wei, X. H.; Xi, C. J. Org. Lett. 2018, 20, 6678.
[49]	Ke, Z. G.; Zhao, Y. F.; Li R. P; Wang, H.; Zeng, W.; Tang, M. H.; Han, B. X.; Liu, Z. M. Green Chem. 2021, 23, 9147.
[50]	Das, A.; Sarkar, P.; Maji, S.; Pati, S. K.; Mandal, S. K. Angew. Chem., Int. Ed. 2022, 61, e202213614.
[51]	Gautam, N.; Logdi, R.; Sreejyothi, P.; Roy, A.; Tiwari, A. K.; Mandal, S. K. Chem. Sci. 2023, 14, 5079.
[52]	Zhao, Y. L.; Liu, X.; Zheng, L. J.; Du, Y. L.; Shi, X. R.; Liu, Y. L.; Yan, Z. Q.; You, J. M.; Jiang, Y. Y. J. Org. Chem. 2020, 85, 912.
[53]	Peng, L. F.; Hu, Z. F.; Wang, H.; Wu, L.; Jiao, Y. C.; Tang, Z. L.; Xu, X. H. RSC Adv. 2020, 10, 10232.
[54]	Wang, H.; Dong, Y. N.; Zheng, C. N.; Sandoval, C. A.; Wang, X.; Makha, M.; Li, Y. H. Chem 2018, 4, 2883.
[55]	Dong, Y. N.; Yang, P. J.; Zhao, S. Z.; Li, Y. H. Nat. Commun. 2020, 11, 4096.
[56]	Sahoo, P. K.; Zhang, Y.; Das, S. ACS Catal. 2021, 11, 3414.
[57]	Schilling, W.; Das, S. Tetrahedron Lett. 2018, 59, 3821.
[58]	Fauziev, R. V.; Ivanov, R. E.; Kuchurov, I. V.; Zlotin, S. G. Green Chem. 2021, 23, 10137.
[59]	Shiozuka, A.; Sekine, K.; Kuninobu, Y. Org. Lett. 2021, 23, 4774. doi: 10.1021/acs.orglett.1c01503 pmid: 34097411

二氧化碳参与的三组分偶联反应进展

Advances in Three-Component Coupling Reactions Involving CO₂

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