多组分反应策略将二氧化碳固定为氨基甲酸酯的研究进展

doi:10.1016/S1872-2067(21)64029-9

摘要/Abstract

摘要：

二氧化碳是主要的温室气体, 也是地球上储量最丰富、廉价易得的碳一资源, 具有无毒、不燃和可循环使用等优点. 发展将二氧化碳转化为各种高附加值化学品的新方法、新策略, 引起了人们的极大兴趣. 但由于其化学性质稳定, 实现二氧化碳在温和条件下的活化仍然具有极大挑战性.

氨基甲酸酯是许多具有生物活性的天然产物和药物的重要骨架, 也是重要的化工原料、合成中间体, 在有机合成中具有广泛的应用. 传统的氨基甲酸酯合成方法以光气或异氰酸酯类化合物为原料, 但由于光气或异氰酸酯类化合物毒性高, 容易造成环境污染, 威胁人类的身体健康, 所以使用受到极大限制. 过去几十年, 人们相继开发出一些非光气合成氨基甲酸酯的方法, 如硝基芳烃的还原羰基化、胺的氧化羰基化、Hofmann和Curtius重排反应等, 但这些方法存在反应条件苛刻、底物适用性不广等问题. 因此, 发展更加高效绿色的氨基甲酸酯合成新方法十分必要. 而利用二氧化碳替代光气来合成氨基甲酸酯化合物无疑具有很多优势, 因此受到各国化学家的广泛关注.

近十年来, 二氧化碳化学转化为氨基甲酸酯的研究取得很多新进展, 其中通过多组分策略构建氨基甲酸酯化合物的研究格引人关注. 利用二氧化碳非常容易和有机胺作用形成具有亲核性的氨基甲酸根阴离子这一性质, 人们发展出一系列新的构建氨基甲酸酯(包括环状和非环状氨基甲酸酯)的多组分反应. 合成非环状氨基甲酸酯策略包括亲核试剂与亲电试剂的偶联反应、亲核试剂与亲核试剂的氧化偶联反应、不饱和烃的双功能化反应以及碳氢键的功能化反应等; 而成环状氨基甲酸酯的策略包括原位生成不饱和胺的羰化环化反应和不饱和胺的羰化环化双功能化反应.

本论文根据氨基甲酸酯的种类和合成策略对该领域近十年的研究进展进行了系统的总结. 分析了目前利用二氧化碳合成氨基甲酸酯领域面临的问题和挑战, 包括新催化体系的研发、新反应策略以及手性氨基甲酸酯分子的构建等, 并对未来的发展趋势进行了展望.

关键词: 二氧化碳, 胺, 氨基甲酸酯, 多组分反应, 合成策略

Abstract:

Carbon dioxide (CO₂) is the main greenhouse gas and also an ideal C1 feedstock in organic synthesis because it is abundant, non-toxic, nonflammable, and renewable. The synthesis of organic carbamates using CO₂ as a phosgene alternative has attracted extensive attention because of the importance of carbamates in organic synthesis and in the pharmaceutical and agrochemical industries. In recent decades, many multicomponent reaction strategies have been designed for constructing different types of organic carbamate molecules. Most of these methods rely on the in situ generation of carbamate anions from CO₂ and amines, followed by reactions with other coupling partners. Synthetic strategies for acyclic carbamates include nucleophile-electrophile coupling, nucleophile-nucleophile oxidative coupling, difunctionalization of unsaturated hydrocarbons, and C-H bond functionalization. Strategies for the synthesizing cyclic carbamates include carboxylative cyclization of in situ-generated unsaturated amines and difunctionalization of unsaturated amines with CO₂ and other electrophilic reagents. This review summarizes the recent advances in the synthesis of organic carbamates from CO₂ using different multicomponent reaction strategies. Future perspectives and challenges in the incorporation of CO₂ into carbamates are also presented.

Key words: Carbon dioxide, Amines, Carbamate, Multicomponent reaction, Synthetic strategy

汪露, 戚朝荣, 熊文芳, 江焕峰. 多组分反应策略将二氧化碳固定为氨基甲酸酯的研究进展[J]. 催化学报, 2022, 43(7): 1598-1617.

Lu Wang, Chaorong Qi, Wenfang Xiong, Huanfeng Jiang. Recent advances in fixation of CO₂into organic carbamates through multicomponent reaction strategies[J]. Chinese Journal of Catalysis, 2022, 43(7): 1598-1617.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(21)64029-9

https://www.cjcatal.com/CN/Y2022/V43/I7/1598

图/表 44

Scheme 1. Representative carbamate-bearing molecules and traditional methods for synthesizing organic carbamates.

Scheme 2. Reaction pathways for the synthesis of acyclic carbamates with CO2.

Scheme 3. Strategies for synthesizing acyclic carbamates from CO2 via carbamate anion intermediate.

Scheme 4. PEG-promoted synthesis of carbamates from alkyl halides, CO2, and amines.

Scheme 5. Cs2CO3-promoted coupling of alkyl halides, CO2, and amines.

Scheme 6. Cs2CO3-promoted coupling of phenacyl bromide with CO2 and amines.

Scheme 7. Cs2CO3-promoted synthesis of nitrile-containing carbamates.

Scheme 8. Ir-catalyzed enantioselective coupling of allyl chlorides, CO2, and amines.

Scheme 9. Pd-catalyzed coupling of allyl chlorides, CO2, and amines.

Scheme 10. CaC2-promoted coupling of alcohols, amines, and CO2.

Scheme 11. Au/Fe2O3-catalyzed coupling CO2, epoxides, and amines.

Scheme 12. K2CO3-promoted coupling of CO2, amines, and N-tosylhydrazones.

Scheme 13. Ag-catalyzed coupling of CO2, amines and α-diazoesters.

Scheme 14. Visible-light-driven coupling of CO2, amines, and α-diazoesters.

Scheme 15. Ir-catalyzed coupling between CO2, amines, and sulfoxonium ylides.

Scheme 16. DBU-promoted coupling of CO2, amines, and diaryliodonium salts.

Scheme 17. Cu-catalyzed oxidative coupling of CO2, amines, and arylboronic acids.

Scheme 18. Ru-catalyzed synthesis of vinyl carbamate from CO2 and alkynes.

Scheme 19. Ag-catalyzed coupling of CO2, amines, and aryloxyallenes.

Scheme 20. Pd-catalyzed coupling of allenyl ethers, aryl iodides, amines, and CO2.

Scheme 21. Pd-catalyzed regioselective coupling of CO2, amines, and allenes.

Scheme 22. Cu-catalyzed coupling of enynes, Togni’s reagent, CO2, and amines.

Scheme 23. Cu-catalyzed coupling of akenes, CO2, amines, and Togni’s reagent.

Scheme 24. TBAI-mediated coupling of 3-triflyloxybenzynes, cyclic ethers, amines, and CO2.

Scheme 25. Photocatalytic coupling of ethynylbenziodoxolones, CO2, and amines.

Scheme 26. TBAI-catalyzed oxidative coupling of aryl ketones, amines, and CO2.

Scheme 27. Cu-catalyzed coupling of amines, CO2, and pincer-like arenes.

Scheme 28. Cu-catalyzed coupling of aryl carboxamides, amines, and CO2.

Scheme 29. Strategies for the synthesis of cyclic carbamates from CO2 via multicomponent reaction.

Scheme 30. Cu-catalyzed coupling of aldehydes, terminal alkynes, amines, and CO2.

Scheme 31. CuI/SnCl2-cocatalyzed coupling of ketones, amines, alkynes, and CO2.

Scheme 32. Tandem reaction for the synthesis of chiral oxazolidinones.

Scheme 33. Ag-catalyzed coupling of N-iodosuccinimide, propargylic amines, and CO2.

Scheme 34. Pd-catalyzed coupling of propargylic amines, aryl halides, and CO2.

Scheme 35. Pd/Cu-catalyzed coupling of propargylic amides, aryl halides, and CO2.

Scheme 36. Metal-free coupling of unsaturated amines with t-BuOI and CO2.

Scheme 37. Cu-catalyzed oxy-trifluoromethylation of allylamines with CO2 and Togni’s reagent.

Scheme 38. Cu-catalyzed dearomatization of indoles and furans with Togni’s reagent and CO2.

Scheme 39. Cu-catalyzed oxy-cyanoalkylation of allylamines with cycloketone oxime esters and CO2.

Scheme 40. Visible-light-driven oxy-perfluoroalkylation of allylic amines with CO2 and perfluoroalkyl iodides.

Scheme 41. Visible-light-driven oxy-difluoroalkylation of allylic amines with CO2.

Scheme 42. Visible-light-driven Pd-catalyzed oxy-alkylation of allylic amines with alkyl bromides and CO2.

Scheme 43. Pd-catalyzed oxy-alkylation of 2,3-allenic amines, organic iodides, and CO2.

Scheme 44. Visible-light-driven Pd-catalyzed oxy-alkylation of 2-(1-arylvinyl)anilines with CO2 and alkyl bromides.

参考文献

[1]	K. Sekine, T. Yamada, Chem. Soc. Rev., 2016, 45, 4524-4532.
[2]	Q.-W. Song, Z.-H. Zhou, L.-N. He, Green Chem., 2017, 19, 3707-3728.
[3]	Y. Cao, X. He, N. Wang, H.-R. Li, L.-N. He, Chin. J. Chem., 2018, 36, 644-659.
[4]	V. A. Peshkov, O. P. Pereshivko, A. A. Nechaev, A. A. Peshkov, E. V. Van der Eycken, Chem. Soc. Rev., 2018, 47, 3861-3898.
[5]	A. Tortajada, F. Julia-Hernandez, M. Borjesson, T. Moragas, R. Martin, Angew. Chem. Int. Ed., 2018, 57, 15948-15982.
[6]	S.-S. Yan, Q. Fu, L.-L. Liao, G.-Q. Sun, J.-H. Ye, L. Gong, Y.-Z. Bo-Xue, D.-G. Yu, Coord. Chem. Rev., 2018, 374, 439-463.
[7]	B. Grignard, S. Gennen, C. Jerome, A. W. Kleij, C. Detrembleur, Chem. Soc. Rev., 2019, 48, 4466-4514.
[8]	S. Wang, C. Xi, Chem. Soc. Rev., 2019, 48, 382-404.
[9]	C. S. Yeung, Angew. Chem. Int. Ed., 2019, 58, 5492-5502.
[10]	K. Chen, H. Li, L. He, Chin. J. Org. Chem., 2020, 40, 2195-2207.
[11]	X. Guo, Y. Wang, J. Chen, G. Li, J.-B. Xia, Chin. J. Org. Chem., 2020, 40, 2208-2220.
[12]	C. Zhou, M. Li, J. Yu, S. Sun, J. Cheng, Chin. J. Org. Chem., 2020, 40, 2221-2231.
[13]	C.-K. Ran, X.-W. Chen, Y.-Y. Gui, J. Liu, L. Song, K. Ren, D.-G. Yu, Sci. China Chem., 2020, 63, 1336-1351.
[14]	H. J. Ma, R. L. Xie, Q. F. Zhao, X. D. Mei, J. Ning, J. Agric. Food Chem., 2010, 58, 12817-12821.
[15]	C. M. Pavlik, C. Y. B. Wong, S. Ononye, D. D. Lopez, N. Engene, K. L. McPhail, W. H. Gerwick, M. J. Balunas, J. Nat. Prod., 2013, 76, 2026-2033.
[16]	C.-D. Pham, R. Hartmann, P. Böhler, B. Stork, S. Wesselborg, W. Lin, D. Lai, P. Proksch, Org. Lett., 2013, 16, 266-269.
[17]	A. K. Ghosh, M. Brindisi, J. Med. Chem., 2015, 58, 2895-2940.
[18]	P. Salisaeng, P. Arnnok, N. Patdhanagul, R. Burakham, J. Agric. Food Chem., 2016, 64, 2145-2152.
[19]	S. Hara, N. Ishikawa, Y. Hara, T. Nehira, K. Sakai, T. Gonoi, M. Ishibashi, J. Nat. Prod., 2017, 80, 565-568.
[20]	A. D. Marchese, M. Wollenburg, B. Mirabi, X. Abel-Snape, A. Whyte, F. Glorius, M. Lautens, ACS Catal., 2020, 10, 4780-4785.
[21]	A. Berkessel, Angew. Chem. Int. Ed., 2008, 47, 3677-3679.
[22]	X. Zhao, C. S. Yeung, V. M. Dong, J. Am. Chem. Soc., 2010, 132, 5837-5844.
[23]	M. R. Harris, L. E. Hanna, M. A. Greene, C. E. Moore, E. R. Jarvo, J. Am. Chem. Soc., 2013, 135, 3303-3306.
[24]	D. Holt, M. J. Gaunt, Angew. Chem. Int. Ed., 2015, 54, 7857-7861.
[25]	Y. Wang, S. B. Wu, W. J. Shi, Z. J. Shi, Org. Lett., 2016, 18, 2548-2551.
[26]	T. Li, J. Zhang, C. Yu, X. Lu, L. Xu, G. Zhong, Chem. Commun., 2017, 53, 12926-12929.
[27]	Z. Chen, C. M. So, Org. Lett., 2020, 22, 3879-3883.
[28]	S. Ozaki, Chem. Rev., 1972, 72, 457-496.
[29]	H. Babad, A. G. Zeiler, Chem. Rev., 1973, 73, 75-91.
[30]	A. M. Tafesh, J. Weiguny, Chem. Rev., 1996, 96, 2035-2052.
[31]	F. Shi, Y. Deng, Chem. Commun., 2001, 443-444.
[32]	H. Lebel, O. Leogane, Org. Lett., 2005, 7, 4107-4110.
[33]	H. Lebel, O. Leogane, Org. Lett., 2006, 8, 5717-5720.
[34]	A. Yoshimura, M. W. Luedtke, V. V. Zhdankin, J. Org. Chem., 2012, 77, 2087-2091.
[35]	W. Ali, S. K. Rout, S. Guin, A. Modi, A. Banerjee, B. K. Patel, Adv. Synth. Catal., 2015, 357, 515-522.
[36]	G. S. Kumar, C. U. Maheswari, R. A. Kumar, M. L. Kantam, K. R. Reddy, Angew. Chem. Int. Ed., 2011, 50, 11748-11751.
[37]	N. T. S. Phan, T. T. Nguyen, P. H. L. Vu, ChemCatChem, 2013, 5, 3068-3077.
[38]	D. Chaturvedi, Tetrahedron, 2012, 68, 15-45.
[39]	E. Vessally, R. Mohammadi, A. Hosseinian, L. Edjlali, M. Babazadeh, J. CO₂ Util., 2018, 24, 361-368.
[40]	W. Schilling, S. Das, ChemSusChem, 2020, 13, 6246-6258.
[41]	T.-K. Xiong, X.-J. Li, M. Zhang, Y. Liang, Org. Biomol. Chem., 2020, 18, 7774-7788.
[42]	Q. W. Song, Z. H. Zhou, H. Yin, L.-N. He, ChemSusChem, 2015, 8, 3967-3972.
[43]	D. Song, D. Li, X. Xiao, C. Cheng, S. Chaemchuen, Y. Yuan, F. Verpoort,J. CO₂ Util., 2018, 27, 217-222.
[44]	N. Germain, I. Muller, M. Hanauer, R. A. Paciello, R. Baumann, O. Trapp, T. Schaub, ChemSusChem, 2016, 9, 1586-1590.
[45]	W. Guo, V. Laserna, J. Rintjema, A. W. Kleij, Adv. Synth. Catal., 2016, 358, 1602-1607.
[46]	A. K. Ghosh, M. Brindisi, J. Med. Chem., 2015, 58, 2895-2940.
[47]	K. Tomishige, M. Tamura, Y. Nakagawa, Chem. Rec., 2019, 19, 1354-1379.
[48]	Q. Zhang, H.-Y. Yuan, N. Fukaya, H. Yasuda, J.-C. Choi, ChemSusChem, 2017, 10, 1501-1508.
[49]	Q. Zhang, H.-Y. Yuan, N. Fukaya, H. Yasuda, J.-C. Choi, Green Chem., 2017, 19, 5614-5624.
[50]	D.-L. Kong, L.-N. He, J.-Q. Wang, Synth. Commun., 2011, 41, 3298-3307.
[51]	D. Riemer, P. Hirapara, S. Das, ChemSusChem, 2016, 9, 1916-1920.
[52]	E. Speckmeier, M. Klimkait, K. Zeitler, J. Org. Chem., 2018, 83, 3738-3745.
[53]	L. Yang, L. Fu, G. Li, Adv. Synth. Catal., 2017, 359, 2235-2240.
[54]	M. Zhang, X. Zhao, S. Zheng, Chem. Commun., 2014, 50, 4455-4458.
[55]	J. Cai, M. Zhang, X. Zhao, Eur. J. Org. Chem., 2015, 2015, 5925-5928.
[56]	Q. Zhang, H.-Y. Yuan, X.-T. Lin, N. Fukaya, T. Fujitani, K. Sato, J.-C. Choi, Green Chem., 2020, 22, 4231-4239.
[57]	Z. Zhang, S. Liu, L. Zhang, S. Yin, G. Yang, B. Han, Chem. Commun., 2018, 54, 4410-4412.
[58]	A. Hosseinian, S. Ahmadi, R. Mohammadi, A. Monfared, Z. Rahmani, J. CO₂ Util., 2018, 27, 381-389.
[59]	J. Shang, X. Guo, Z. Li, Y. Deng, Green Chem., 2016, 18, 3082-3088.
[60]	S. S. Yan, L. Zhu, J. H. Ye, Z. Zhang, H. Huang, H. Zeng, C. J. Li, Y. Lan, D. G. Yu, Chem. Sci., 2018, 9, 4873-4878.
[61]	H. Xiong, X. Wu, H. Wang, S. Sun, J. T. Yu, J. Cheng, Adv. Synth. Catal., 2019, 361, 3538-3542.
[62]	S. Wang, B.-Y. Cheng, M. Sršen, B. König, J. Am. Chem. Soc., 2020, 142, 7524-7531.
[63]	W. Xiong, C. Qi, H. He, L. Ouyang, M. Zhang, H. Jiang, Angew. Chem. Int. Ed., 2015, 54, 3084-3087.
[64]	J. Y. Hong, U. R. Seo, Y. K. Chung, Org. Chem. Front., 2016, 3, 764-767.
[65]	C. Qi, D. Yan, W. Xiong, H. Jiang, Chin. J. Chem., 2018, 36, 399-405.
[66]	R. Cheng, C. Qi, L. Wang, W. Xiong, H. Liu, H. Jiang, Green Chem., 2020, 22, 4890-4895.
[67]	H. Jiang, H. Zhang, W. Xiong, C. Qi, W. Wu, L. Wang, R. Cheng, Org. Lett., 2019, 21, 1125-1129.
[68]	W. Xiong, C. Qi, Y. Peng, T. Guo, M. Zhang, H. Jiang, Chem. Eur. J., 2015, 21, 14314-14318.
[69]	W. Xiong, C. Qi, T. Guo, M. Zhang, K. Chen, H. Jiang, Green Chem., 2017, 19, 1642-1646.
[70]	Y. Sasaki, P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1986, 790-791.
[71]	Y. Sasaki, P. H. Dixneuf, J. Org. Chem., 1987, 52, 4389-4391.
[72]	M. Rohr, C. Geyer, R. Wandeler, M. S. Schneider, E. F. Murphy, A. Baiker, Green Chem., 2001, 3, 123-125.
[73]	Y. P. Patil, P. J. Tambade, N. S. Nandurkar, B. M. Bhanage, Catal. Commun., 2008, 9, 2068-2072.
[74]	R. A. Watile, B. M. Bhanage, RSC Adv., 2014, 4, 23022-23026.
[75]	C. Qi, D. Yan, W. Xiong, H. Jiang, J. CO₂ Util., 2018, 24, 120-127.
[76]	W. Xiong, D. Yan, C. Qi, H. Jiang, Org. Lett., 2018, 20, 672-675.
[77]	W. Xiong, R. Cheng, B. Wu, W. Wu, C. Qi, H. Jiang, Sci. China Chem., 2020, 63, 331-335.
[78]	L. Wang, C. Qi, R. Cheng, H. Liu, W. Xiong, H. Jiang, Org. Lett., 2019, 21, 7386-7389.
[79]	L. Wang, P. Wang, T. Guo, W. Xiong, B. Kang, C. Qi, G. Luo, Y. Luo, H. Jiang, Org. Chem. Front., 2021, 8, 1851-1857.
[80]	H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc., 2006, 128, 11040-11041.
[81]	H. Yoshida, T. Morishita, J. Ohshita, Org. Lett., 2008, 10, 3845-3847.
[82]	T. Kaicharla, M. Thangaraj, A. T. Biju, Org. Lett., 2014, 16, 1728-1731.
[83]	W.-J. Yoo, T. V. Q. Nguyen, S. Kobayashi, Angew. Chem. Int. Ed., 2014, 53, 10213-10217.
[84]	W. Xiong, C. Qi, R. Cheng, H. Zhang, L. Wang, D. Yan, H. Jiang, Chem. Commun., 2018, 54, 5835-5838.
[85]	Y. Li, D. P. Hari, M. V. Vita, and J. Waser, Angew. Chem. Int. Ed., 2016, 55, 4436-4454.
[86]	D. P. Hari, P. Caramenti, J. Waser, Acc. Chem. Res., 2018, 51, 3212-3225.
[87]	L. Wang, F. Shi, C. Qi, W. Xu, W. Xiong, B. Kang, H. Jiang, Chem. Sci., 2021, 12, 11821-11830.
[88]	Y. Peng, J. Liu, C. Qi, G. Yuan, J. Li, H. Jiang, Chem. Commun., 2017, 53, 2665-2668.
[89]	J. Wang, P. Qian, K. Hu, Z. Zha, Z. Wang, ChemElectroChem, 2019, 6, 4292-4705.
[90]	E. Bernoud, A. Company, X. Ribas, J. Organometal. Chem., 2017, 845, 44-48.
[91]	X. Luo, X. Song, W. Xiong, J. Li, M. Li, Z. Zhu, S. Wei, A. S. C. Chan, Y. Zou, Org. Lett., 2019, 21, 2013-2018.
[92]	Y. Kayaki, M. Yamamoto, T. Suzuki, T. Ikariya, Green Chem., 2006, 8, 1019-1021.
[93]	S. Hase, Y. Kayaki, T. Ikariya, ACS Catal., 2015, 5, 5135-5140.
[94]	P. Brunel, J. Monot, C.E. Kefalidis, L. Maron, B. Martin-Vaca, D. Bourissou, ACS Catal., 2017, 7, 2652-2660.
[95]	L. Soldi, C. Massera, M. Costa, N. Della Ca’ Tetrahedron Lett., 2014, 55, 1379-1383.
[96]	Y. Kayaki, N. Mori, T. Ikariya, Tetrahedron Lett., 2009, 50, 6491-6493.
[97]	K. Yamashita, S. Hase, Y. Kayaki, T. Ikariya, Org. Lett., 2015, 17, 2334-2337.
[98]	W.-J. Yoo, C.-J. Li, Adv. Synth. Catal., 2008, 350, 1503-1506.
[99]	J. Zhao, H. Huang, C. Qi, H. Jiang, Eur. J. Org. Chem., 2012, 2012, 5665-5667.
[100]	X.-T. Gao, C.-C. Gan, S.-Y. Liu, F. Zhou, H.-H. Wu, J. Zhou, ACS Catal., 2017, 7, 8588-8593.
[101]	S. Kikuchi, S. Yoshida, Y. Sugawara, W. Yamada, H.-M. Cheng, K. Fukui, K. Sekine, I. Iwakura, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn., 2011, 84, 698-717.
[102]	K. Sekine, R. Kobayashi, T. Yamada, Chem. Lett., 2015, 44, 1407-1409.
[103]	P. García-Domínguez, L. Fehr, G. Rusconi, C. Nevado, Chem. Sci., 2016, 7, 3914-3918.
[104]	C. Zhou, Y. Dong, J.-T. Yu, S. Sun, J. Cheng, Chem. Commun., 2019, 55, 13685-13688.
[105]	Y. Takeda, S. Okumura, S. Tone, I. Sasaki, S. Minakata, Org. Lett., 2012, 14, 4874-4877.
[106]	J.-H. Ye, L. Song, W.-J. Zhou, T. Ju, Z.-B. Yin, S.-S. Yan, Z. Zhang, J. Li, D.-G. Yu, Angew. Chem. Int. Ed., 2016, 55, 10022-10026.
[107]	J.-H. Ye, L. Zhu, S.-S. Yan, M. Miao, X.-C. Zhang, W.-J. Zhou, J. Li, Y. Lan, D.-G. Yu, ACS Catal., 2017, 7, 8324-8330.
[108]	C.-K. Ran, H. Huang, X.-H. Li, W. Wang, J.-H. Ye, S.-S. Yan, B.-Q. Wang, C. Feng, D.-G. Yu, Chin. J. Chem., 2020, 38, 69-76.
[109]	M.-Y. Wang, Y. Cao, X. Liu, N. Wang, L.-N. He, S.-H. Li, Green Chem., 2017, 19, 1240-1244.
[110]	Z.-B. Yin, J.-H. Ye, W.-J. Zhou, Y.-H. Zhang, L. Ding, Y.-Y. Gui, S.-S. Yan, J. Li, D.-G. Yu, Org. Lett., 2018, 20, 190-193.
[111]	L. Sun, J.-H. Ye, W.-J. Zhou, X. Zeng, D.-G. Yu, Org. Lett., 2018, 20, 3049-3052.
[112]	S. Li, J. Ye, W. Yuan, S. Ma, Tetrahedron, 2013, 69, 10450-10456.
[113]	S. Sun, C. Zhou, J.-T. Yu, J. Cheng, Org. Lett., 2019, 21, 6579-6583.
[114]	S. Xie, Q. Zhang, G. Liu, Y. Wang, Chem. Commun., 2016, 52, 35-59.
[115]	X. He, L.-Q. Qiu, W.-J. Wang, K.-H. Chen, L.-N. He, Green Chem., 2020, 22, 7301-7320.
[116]	Z. Zhang, J.-H. Ye, T. Ju, L.-L. Liao, H. Huang, Y.-Y. Gui, W.-J. Zhou, D.-G. Yu, ACS Catal., 2020, 10, 10871-10885.
[117]	B. Cai, H. W. Cheo, T. Liu, J. Wu, Angew. Chem. Int. Ed., 2021, 60, 18950-18980.
[118]	U. Ulmer, T. Dingle, P. N. Duchesne, R. H. Morris, A. Tavasoli, T. Wood, G. A. Ozin, Nat. Commun., 2019, 10, 3169.
[119]	J. Vaitla, Y. Guttormsen, J. K. Mannisto, A. Nova, T. Repo, A. Bayer, K. H. Hopmann, ACS Catal., 2017, 7, 7231-7244.