二氧化碳转化为氨基甲酸酯的研究进展

引用本文: 郭艳辉, 魏丽, 温中林, 戚朝荣, 江焕峰. 二氧化碳转化为氨基甲酸酯的研究进展[J]. 物理化学学报, 2024, 40(4): 230700. doi: 10.3866/PKU.WHXB202307004 shu

Citation: Yanhui Guo, Li Wei, Zhonglin Wen, Chaorong Qi, Huanfeng Jiang. Recent Progress on Conversion of Carbon Dioxide into Carbamates[J]. Acta Physico-Chimica Sinica, 2024, 40(4): 230700. doi: 10.3866/PKU.WHXB202307004 shu

二氧化碳转化为氨基甲酸酯的研究进展

华南理工大学化学与化工学院, 广东省功能分子工程重点实验室, 广州 510641

通讯作者: 戚朝荣,Email:crqi@scut.edu.cn; 江焕峰,Email:jianghf@scut.edu.cn

基金项目:
国家重点研发计划(2022YFB4101800),国家自然科学基金(21971073,22271098),广东省自然科学基金(2019A1515011468)资助项目

摘要: 二氧化碳(CO₂)是大气中主要的温室气体，同时也是一种丰富、无毒和可再生的碳一资源。因此，将CO₂转化为有价值的化学品对实现可持续发展具有重要意义。然而，由于CO₂的热力学稳定性和动力学惰性，其活化转化非常具有挑战性。氨基甲酸酯是一类具有生物活性的重要化合物，广泛存在于天然产物、农用化学品和医药相关分子中，同时也是重要的有机合成中间体。近年来，利用CO₂作为光气的替代品用于合成氨基甲酸酯吸引了广泛的关注。本文主要综述了CO₂和胺在不同的催化体系下合成氨基甲酸酯的最新研究进展，主要分为无过渡金属催化、过渡金属催化、电催化、光催化四种反应体系来归纳总结，并对CO₂转化为氨基甲酸酯的未来研究方向进行了展望。

关键词:

English

Recent Progress on Conversion of Carbon Dioxide into Carbamates

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China

Corresponding author: Chaorong Qi, ; Huanfeng Jiang,

Received Date: 03 July 2023
Accepted Date: 01 August 2023
Revised Date: 01 August 2023
Available Online: 07 August 2023
Fund Project:
The project was supported by the National Key Research and Development Program of China (2022YFB4101800), the National Natural Science Foundation of China (21971073, 22271098), the Natural Science Foundation of Guangdong Province, China (2019A1515011468).

Abstract: Carbon dioxide (CO₂) serves as one of the major greenhouse gases in the atmosphere. However, it is also abundant, non-toxic, and renewable, making it a valuable one-carbon source. Therefore, converting CO₂ into valuable chemicals holds immense significance as an effective approach towards achieving carbon neutrality. Nevertheless, due to CO₂’s thermodynamic stability and kinetic inertness, its activation and conversion present considerable challenges. Organic carbamates, both cyclic and acyclic, represent a crucial class of bioactive compounds found in various natural products, agricultural chemicals, and pharmaceutically relevant molecules. They are also widely used as essential intermediates in organic synthesis. Unfortunately, traditional methods for preparing organic carbamates often rely on highly toxic phosgene and its derivatives as raw materials, posing serious environmental and safety concerns and limiting practical applications. From a cost-effective and sustainable standpoint, substituting CO₂ for phosgene in the synthesis of organic carbamates is highly appealing. In recent decades, numerous new reactions, particularly multicomponent reactions involving CO₂ and amines, have emerged, providing efficient methods for constructing diverse and valuable carbamates. Some of these reactions can be conducted under transition-metal-free conditions, utilizing organic and inorganic bases, ionic liquids, or small organic molecules as catalysts or promoters. However, in certain cases, transition-metal catalysts, such as those based on copper, palladium, or silver, are required, especially when the reactions involve activating unsaturated hydrocarbons like alkenes and alkynes. Mechanistically, most of these methods involve in situ generation of nucleophilic CO₂-amine adducts, such as carbamate salts or carbamic acids, which then react with other electrophiles or coupling partners to yield the desired carbamates. Notably, recent advancements have led to the successful development of several elegant methods for synthesizing specific types of carbamates using electrocatalysis or photocatalysis, which are not achievable through conventional thermal catalysis. This review comprehensively summarizes the recent progress in the synthesis of organic carbamates using CO₂ and amines under various catalytic conditions, including transition metal-free conditions, transition metal-catalysis, electrocatalysis, and photocatalysis. Additionally, the review discusses the challenges and future prospects associated with converting CO₂ into organic carbamates.

Key words:

1. [1]
  (1) Yu, D. Y.; Teong, S. P.; Zhang, Y. G. Coord. Chem. Rev. 2015, 293, 279. doi: 10.1016/j.ccr.2014.09.002(1) Yu, D. Y.; Teong, S. P.; Zhang, Y. G. Coord. Chem. Rev. 2015, 293, 279. doi: 10.1016/j.ccr.2014.09.002
2. [2]
  (2) Börjesson, M.; Moragas, T.; Gallego, D.; Martin, R. ACS Catal. 2016, 6, 6739. doi: 10.1021/acscatal.6b02124(2) Börjesson, M.; Moragas, T.; Gallego, D.; Martin, R. ACS Catal. 2016, 6, 6739. doi: 10.1021/acscatal.6b02124
3. [3]
  (3) Sekine, K.; Yamada, T. Chem. Soc. Rev. 2016, 45, 4524. doi: 10.1039/C5CS00895F(3) Sekine, K.; Yamada, T. Chem. Soc. Rev. 2016, 45, 4524. doi: 10.1039/C5CS00895F
4. [4]
  (4) Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861. doi: 10.1039/C7CS00065K(4) Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861. doi: 10.1039/C7CS00065K
5. [5]
  (5) Yan, S.-S.; Fu, Q.; Liao, L.-L.; Sun, G. Q.; Ye, J.-H.; Gong, L.; Bo-Xue, Y.-Z.; Yu, D.-G. Coord. Chem. Rev. 2018, 374, 439. doi: 10.1016/j.ccr.2018.07.011(5) Yan, S.-S.; Fu, Q.; Liao, L.-L.; Sun, G. Q.; Ye, J.-H.; Gong, L.; Bo-Xue, Y.-Z.; Yu, D.-G. Coord. Chem. Rev. 2018, 374, 439. doi: 10.1016/j.ccr.2018.07.011
6. [6]
  (6) Grignard, B.; Gennen, S.; Jérôme, C.; Kleij, A. W.; Detrembleur, C. Chem. Soc. Rev. 2019, 48, 4466. doi: 10.1039/c9cs00047j(6) Grignard, B.; Gennen, S.; Jérôme, C.; Kleij, A. W.; Detrembleur, C. Chem. Soc. Rev. 2019, 48, 4466. doi: 10.1039/c9cs00047j
7. [7]
  (7) Wang, S.; Xi, C. Chem. Soc. Rev. 2019, 48, 382. doi: 10.1039/C8CS00281A(7) Wang, S.; Xi, C. Chem. Soc. Rev. 2019, 48, 382. doi: 10.1039/C8CS00281A
8. [8]
  (8) Yeung, C. S. Angew. Chem. Int. Ed. 2019, 58, 5492. doi: 10.1002/anie.201806285(8) Yeung, C. S. Angew. Chem. Int. Ed. 2019, 58, 5492. doi: 10.1002/anie.201806285
9. [9]
  (9) Chen, K.; Li, H.; He, L. Chin. J. Org. Chem. 2020, 40, 2195. doi: 10.6023/cjoc202004030(9) Chen, K.; Li, H.; He, L. Chin. J. Org. Chem. 2020, 40, 2195. doi: 10.6023/cjoc202004030
10. [10]
  (10) Ran, C.-K.; Chen, X.-W.; Gui, Y.-Y.; Liu, J.; Song, L.; Ren, K.; Yu, D.-G. Sci. China Chem. 2020, 63, 1336. doi: 10.1007/s11426-020-9788-2(10) Ran, C.-K.; Chen, X.-W.; Gui, Y.-Y.; Liu, J.; Song, L.; Ren, K.; Yu, D.-G. Sci. China Chem. 2020, 63, 1336. doi: 10.1007/s11426-020-9788-2
11. [11]
  (11) Zhang, Z.; Ye, J.-H.; Ju, T.; Liao, L.-L.; Huang, H.; Gui, Y.-Y.; Zhou, W.-J.; Yu, D.-G. ACS Catal. 2020, 10, 10871. doi: 10.1021/acscatal.0c03127(11) Zhang, Z.; Ye, J.-H.; Ju, T.; Liao, L.-L.; Huang, H.; Gui, Y.-Y.; Zhou, W.-J.; Yu, D.-G. ACS Catal. 2020, 10, 10871. doi: 10.1021/acscatal.0c03127
12. [12]
  (12) Tortajada, A.; Börjesson, M.; Martin. R. Acc. Chem. Res. 2021, 54, 3941. doi: 10.1021/acs.accounts.1c00480(12) Tortajada, A.; Börjesson, M.; Martin. R. Acc. Chem. Res. 2021, 54, 3941. doi: 10.1021/acs.accounts.1c00480
13. [13]
  (13) Ghosh, A. K.; Brindisi, M. J. Med. Chem. 2015, 58, 2895. doi: 10.1021/jm501371s(13) Ghosh, A. K.; Brindisi, M. J. Med. Chem. 2015, 58, 2895. doi: 10.1021/jm501371s
14. [14]
  (14) Salisaeng, P.; Arnnok, P.; Patdhanagul, N.; Burakham, R. J. Agric. Food Chem. 2016, 64, 2145. doi: 10.1021/acs.jafc.5b05437(14) Salisaeng, P.; Arnnok, P.; Patdhanagul, N.; Burakham, R. J. Agric. Food Chem. 2016, 64, 2145. doi: 10.1021/acs.jafc.5b05437
15. [15]
  (15) Hara, S.; Ishikawa, N.; Hara, Y.; Nehira, T.; Sakai, K.; Gonoi, T.; Ishi-bashi, M. J. Nat. Prod. 2017, 80, 565. doi: 10.1021/acs.jnatprod.6b00935(15) Hara, S.; Ishikawa, N.; Hara, Y.; Nehira, T.; Sakai, K.; Gonoi, T.; Ishi-bashi, M. J. Nat. Prod. 2017, 80, 565. doi: 10.1021/acs.jnatprod.6b00935
16. [16]
  (16) Pandey, G.; Khamrai, J.; Mishra, A. Org. Lett. 2018, 20, 166. doi: 10.1021/acs.orglett.7b03537(16) Pandey, G.; Khamrai, J.; Mishra, A. Org. Lett. 2018, 20, 166. doi: 10.1021/acs.orglett.7b03537
17. [17]
  (17) Chiacchio, M. A.; Lanza, G.; Chiacchio, U.; Giofrè, S. V.; Romeo, R.; Iannazzo, D.; Legnani, L. Curr. Med. Chem. 2019, 26, 7337. doi: 10.2174/0929867326666181203130402(17) Chiacchio, M. A.; Lanza, G.; Chiacchio, U.; Giofrè, S. V.; Romeo, R.; Iannazzo, D.; Legnani, L. Curr. Med. Chem. 2019, 26, 7337. doi: 10.2174/0929867326666181203130402
18. [18]
  (18) Marchese, A. D.; Wollenburg, M.; Mirabi, B.; Abel-Snape, X.; Whyte, A.; Glorius, F.; Lautens, M. ACS Catal. 2020, 10, 4780. doi: 10.1021/acscatal.0c00841(18) Marchese, A. D.; Wollenburg, M.; Mirabi, B.; Abel-Snape, X.; Whyte, A.; Glorius, F.; Lautens, M. ACS Catal. 2020, 10, 4780. doi: 10.1021/acscatal.0c00841
19. [19]
  (19) Wang, Y.; Wu, S.-B.; Shi, W.-J.; Shi, Z.-J. Org. Lett. 2016, 18, 2548. doi: 10.1021/acs.orglett.6b00819(19) Wang, Y.; Wu, S.-B.; Shi, W.-J.; Shi, Z.-J. Org. Lett. 2016, 18, 2548. doi: 10.1021/acs.orglett.6b00819
20. [20]
  (20) Tobisu, M.; Yasui, K.; Aihara, Y.; Chatani, N. Angew. Chem. Int. Ed. 2017, 56, 1877. doi: 10.1002/anie.201610409(20) Tobisu, M.; Yasui, K.; Aihara, Y.; Chatani, N. Angew. Chem. Int. Ed. 2017, 56, 1877. doi: 10.1002/anie.201610409
21. [21]
  (21) Guo, W.; Gómez, J. E.; Cristòfol, À.; Xie, J.; Kleij, A. W. Angew. Chem. Int. Ed. 2018, 57, 13735. doi: 10.1002/anie.201805009(21) Guo, W.; Gómez, J. E.; Cristòfol, À.; Xie, J.; Kleij, A. W. Angew. Chem. Int. Ed. 2018, 57, 13735. doi: 10.1002/anie.201805009
22. [22]
  (22) Yasui, K.; Chatani, N.; Tobisu, M. Org. Lett. 2018, 20, 2108. doi: 10.1021/acs.orglett.8b00674(22) Yasui, K.; Chatani, N.; Tobisu, M. Org. Lett. 2018, 20, 2108. doi: 10.1021/acs.orglett.8b00674
23. [23]
  (23) Dindarloo Inaloo, I.; Majnooni, S.; Eslahi, H.; Esmaeilpour, M. ACS Omega 2020, 5, 7406. doi: 10.1021/acsomega.9b04450(23) Dindarloo Inaloo, I.; Majnooni, S.; Eslahi, H.; Esmaeilpour, M. ACS Omega 2020, 5, 7406. doi: 10.1021/acsomega.9b04450
24. [24]
  (24) Tanaka, J.; Shibata, Y.; Joseph, A.; Nogami, J.; Terasawa, J.; Yoshimura R.; Tanaka, K. Chem.-Eur. J. 2020, 26, 5774. doi: 10.1002/chem.202000253(24) Tanaka, J.; Shibata, Y.; Joseph, A.; Nogami, J.; Terasawa, J.; Yoshimura R.; Tanaka, K. Chem.-Eur. J. 2020, 26, 5774. doi: 10.1002/chem.202000253
25. [25]
  (25) Tanaka, J.; Nagashima, Y.; Tanaka, K. Org. Lett. 2020, 22, 7181. doi: 10.1021/acs.orglett.0c02499(25) Tanaka, J.; Nagashima, Y.; Tanaka, K. Org. Lett. 2020, 22, 7181. doi: 10.1021/acs.orglett.0c02499
26. [26]
  (26) Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837. doi: 10.1021/ja100783c(26) Zhao, X.; Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 5837. doi: 10.1021/ja100783c
27. [27]
  (27) Lo, H.-J.; Lin, C.-Y.; Tseng, M.-C.; Chein, R.-J. Angew. Chem. Int. Ed. 2014, 53, 9026. doi: 10.1002/anie.201404495(27) Lo, H.-J.; Lin, C.-Y.; Tseng, M.-C.; Chein, R.-J. Angew. Chem. Int. Ed. 2014, 53, 9026. doi: 10.1002/anie.201404495
28. [28]
  (28) Sun, X.; Sun, Y.; Zhang, C.; Rao, Y. Chem. Commun. 2014, 50, 1262. doi: 10.1039/C3CC47431C(28) Sun, X.; Sun, Y.; Zhang, C.; Rao, Y. Chem. Commun. 2014, 50, 1262. doi: 10.1039/C3CC47431C
29. [29]
  (29) Yu, B.; He, L.-N. ChemSusChem 2015, 8, 52. doi: 10.1002/cssc.201402837(29) Yu, B.; He, L.-N. ChemSusChem 2015, 8, 52. doi: 10.1002/cssc.201402837
30. [30]
  (30) Vessally, E.; Mohammadi, R.; Hosseinian, A.; Edjlali, L.; Babazadeh, M. J. CO₂ Util. 2018, 24, 361. doi: 10.1016/j.jcou.2018.01.015(30) Vessally, E.; Mohammadi, R.; Hosseinian, A.; Edjlali, L.; Babazadeh, M. J. CO₂ Util. 2018, 24, 361. doi: 10.1016/j.jcou.2018.01.015
31. [31]
  (31) Schilling, W.; Das, S. ChemSusChem 2020, 13, 6246. doi: 10.1002/cssc.202002073(31) Schilling, W.; Das, S. ChemSusChem 2020, 13, 6246. doi: 10.1002/cssc.202002073
32. [32]
  (32) Xiong, T.-K.; Li, X.-J.; Zhang, M.; Liang, Y. Org. Biomol. Chem. 2020, 18, 7774. doi: 10.1039/D0OB01590C(32) Xiong, T.-K.; Li, X.-J.; Zhang, M.; Liang, Y. Org. Biomol. Chem. 2020, 18, 7774. doi: 10.1039/D0OB01590C
33. [33]
  (33) Wang, L.; Qi, C.; Xiong, W.; Jiang, H. Chin. J. Catal. 2022, 43, 1598. doi: 10.1016/S1872-2067(21)64029-9(33) Wang, L.; Qi, C.; Xiong, W.; Jiang, H. Chin. J. Catal. 2022, 43, 1598. doi: 10.1016/S1872-2067(21)64029-9
34. [34]
  (34) Leino, E.; Mäki-Arvela, P.; Eränen, K.; Tenho, M.; Murzina, D. Y.; Salmi, T.; Mikkolaa, J.-P. Chem. Eng. J. 2011, 176, 124. doi: 10.1016/j.cej.2011.07.054(34) Leino, E.; Mäki-Arvela, P.; Eränen, K.; Tenho, M.; Murzina, D. Y.; Salmi, T.; Mikkolaa, J.-P. Chem. Eng. J. 2011, 176, 124. doi: 10.1016/j.cej.2011.07.054
35. [35]
  (35) Ma, J.; Song, J. L.; Liu, H. Z.; Liu, J. L.; Zhang, Z. F.; Jiang, T.; Fan, H. L.; Han, B. X. Green Chem. 2012, 14, 1743. doi: 10.1039/C2GC35150A(35) Ma, J.; Song, J. L.; Liu, H. Z.; Liu, J. L.; Zhang, Z. F.; Jiang, T.; Fan, H. L.; Han, B. X. Green Chem. 2012, 14, 1743. doi: 10.1039/C2GC35150A
36. [36]
  (36) Yang, Z.-Z.; Zhao, Y.-N.; He, L.-N.; Gao, J.; Yin, Z.-S. Green Chem. 2012, 14, 519. doi: 10.1039/C2GC16039K(36) Yang, Z.-Z.; Zhao, Y.-N.; He, L.-N.; Gao, J.; Yin, Z.-S. Green Chem. 2012, 14, 519. doi: 10.1039/C2GC16039K
37. [37]
  (37) Roeser, J.; Kailasam, K.; Thomas, A. ChemSusChem 2012, 5, 1793. doi: 10.1002/cssc.201200091(37) Roeser, J.; Kailasam, K.; Thomas, A. ChemSusChem 2012, 5, 1793. doi: 10.1002/cssc.201200091
38. [38]
  (38) Wang, B. S.; Elageed, E. H. M.; Zhang, D.; Yang, S. J.; Wu, S.; Zhang, G. R.; Gao, G. H. ChemCatChem 2014, 6, 278. doi: 10.1002/cctc.201300801(38) Wang, B. S.; Elageed, E. H. M.; Zhang, D.; Yang, S. J.; Wu, S.; Zhang, G. R.; Gao, G. H. ChemCatChem 2014, 6, 278. doi: 10.1002/cctc.201300801
39. [39]
  (39) Wang, B.; Luo, Z.; Elageed, E. H.; Wu, S.; Zhang, Y.; Wu, X.; Xia, F.; Zhang, G.; Gao, G. ChemCatChem 2016, 8, 830. doi: 10.1002/cctc.201500928(39) Wang, B.; Luo, Z.; Elageed, E. H.; Wu, S.; Zhang, Y.; Wu, X.; Xia, F.; Zhang, G.; Gao, G. ChemCatChem 2016, 8, 830. doi: 10.1002/cctc.201500928
40. [40]
  (40) Sadeghzadeh, S. M.; Zhiani, R.; Emrani, S. Catal. Lett. 2018, 148, 119. doi: 10.1007/s10562-017-2217-z(40) Sadeghzadeh, S. M.; Zhiani, R.; Emrani, S. Catal. Lett. 2018, 148, 119. doi: 10.1007/s10562-017-2217-z
41. [41]
  (41) Zhang, W.; Xia, T.; Yang, X.; Lu, X. Chem. Commun. 2015, 51, 6175. doi: 10.1039/C5CC01530H(41) Zhang, W.; Xia, T.; Yang, X.; Lu, X. Chem. Commun. 2015, 51, 6175. doi: 10.1039/C5CC01530H
42. [42]
  (42) Niemi, T.; Fernandez, I.; Steadman, B.; Mannisto, J. K.; Repo, T. Chem. Commun. 2018, 54, 3166. doi: 10.1039/C8CC00636A(42) Niemi, T.; Fernandez, I.; Steadman, B.; Mannisto, J. K.; Repo, T. Chem. Commun. 2018, 54, 3166. doi: 10.1039/C8CC00636A
43. [43]
  (43) Yousefi, R.; Struble, T. J.; Payne, J. L.; Vishe, M.; Schley, N. D.; Johnston, J. N. J. Am. Chem. Soc. 2019, 141, 618. doi: 10.1021/jacs.8b11793(43) Yousefi, R.; Struble, T. J.; Payne, J. L.; Vishe, M.; Schley, N. D.; Johnston, J. N. J. Am. Chem. Soc. 2019, 141, 618. doi: 10.1021/jacs.8b11793
44. [44]
  (44) Kumar, N.; Kulsoom, M.; Shukla, V.; Kumar, D.; Kumar, S.; Tiwari, J.; Dwivedi, N. Environ. Sci. Pollut. Res. 2018, 25, 29505. doi: 10.1007/s11356-018-2993-z(44) Kumar, N.; Kulsoom, M.; Shukla, V.; Kumar, D.; Kumar, S.; Tiwari, J.; Dwivedi, N. Environ. Sci. Pollut. Res. 2018, 25, 29505. doi: 10.1007/s11356-018-2993-z
45. [45]
  (45) Kovaleva, E. L.; Belanova, A. I.; Panova, L. I.; Zakharchenko, A. A. Pharm. Chem. J. 2018, 52, 84. doi: 10.1007/s11094-018-1769-6(45) Kovaleva, E. L.; Belanova, A. I.; Panova, L. I.; Zakharchenko, A. A. Pharm. Chem. J. 2018, 52, 84. doi: 10.1007/s11094-018-1769-6
46. [46]
  (46) Bezrodnykh, E. A.; Vyshivannaya, O. V.; Polezhaev, A. V.; Abramchuk, S. S.; Blagodatskikh, I. V.; Tikhonov, V. E. Int. J. Biol. Macromol. 2020, 155, 979. doi: 10.1016/j.ijbiomac.2019.11.059(46) Bezrodnykh, E. A.; Vyshivannaya, O. V.; Polezhaev, A. V.; Abramchuk, S. S.; Blagodatskikh, I. V.; Tikhonov, V. E. Int. J. Biol. Macromol. 2020, 155, 979. doi: 10.1016/j.ijbiomac.2019.11.059
47. [47]
  (47) Peterson, S. L.; Stucka, S. M.; Dinsmore, C. J. Org. Lett. 2010, 12, 1340. doi: 10.1021/ol100259j(47) Peterson, S. L.; Stucka, S. M.; Dinsmore, C. J. Org. Lett. 2010, 12, 1340. doi: 10.1021/ol100259j
48. [48]
  (48) Zhang, W.-Z.; Ren, X.; Lu, X.-B. Chin. J. Chem. 2015, 33, 610. doi: 10.1002/cjoc.201500011(48) Zhang, W.-Z.; Ren, X.; Lu, X.-B. Chin. J. Chem. 2015, 33, 610. doi: 10.1002/cjoc.201500011
49. [49]
  (49) Xiong, W.; Qi, C.; Peng, Y.; Guo, T.; Zhang, M.; Jiang, H. Chem. Eur. J. 2015, 21, 14314. doi: 10.1002/chem.201502689(49) Xiong, W.; Qi, C.; Peng, Y.; Guo, T.; Zhang, M.; Jiang, H. Chem. Eur. J. 2015, 21, 14314. doi: 10.1002/chem.201502689
50. [50]
  (50) Xiong, W.; Qi, C.; He, H.; Ouyang, L.; Zhang, M.; Jiang, H. Angew. Chem. Int. Ed. 2015, 54, 3084. doi: 10.1002/anie.201410605(50) Xiong, W.; Qi, C.; He, H.; Ouyang, L.; Zhang, M.; Jiang, H. Angew. Chem. Int. Ed. 2015, 54, 3084. doi: 10.1002/anie.201410605
51. [51]
  (51) Riemer, D.; Hirapara, P.; Das, S. ChemSusChem 2016, 9, 1916. doi: 10.1002/cssc.201600521(51) Riemer, D.; Hirapara, P.; Das, S. ChemSusChem 2016, 9, 1916. doi: 10.1002/cssc.201600521
52. [52]
  (52) Peng, Y.; Liu, J.; Qi, C.; Yuan, G.; Li, J.; Jiang, H. Chem. Commun. 2017, 53, 2665. doi: 10.1039/C6CC09762F(52) Peng, Y.; Liu, J.; Qi, C.; Yuan, G.; Li, J.; Jiang, H. Chem. Commun. 2017, 53, 2665. doi: 10.1039/C6CC09762F
53. [53]
  (53) Wang, S.; Zhang, X.; Cao, C.; Chen, C.; Xi, C. Green Chem. 2017, 19, 4515. doi: 10.1039/c7gc01992k(53) Wang, S.; Zhang, X.; Cao, C.; Chen, C.; Xi, C. Green Chem. 2017, 19, 4515. doi: 10.1039/c7gc01992k
54. [54]
  (54) Zhang, Q.; Yuan, H.-Y.; Fukaya, N.; Choi, J.-C. ACS Sustain. Chem. Eng. 2018, 6, 6675. doi: 10.1021/acssuschemeng.8b00449(54) Zhang, Q.; Yuan, H.-Y.; Fukaya, N.; Choi, J.-C. ACS Sustain. Chem. Eng. 2018, 6, 6675. doi: 10.1021/acssuschemeng.8b00449
55. [55]
  (55) Xiong, W.; Qi, C.; Cheng, R.; Zhang, H.; Wang, L.; Yan, D.; Jiang, H. Chem. Commun. 2018, 54, 5835. doi: 10.1039/C8CC01732H(55) Xiong, W.; Qi, C.; Cheng, R.; Zhang, H.; Wang, L.; Yan, D.; Jiang, H. Chem. Commun. 2018, 54, 5835. doi: 10.1039/C8CC01732H
56. [56]
  (56) Franz, M.; Stalling, T.; Steinert, H.; Martens, J. Org. Biomol. Chem. 2018, 16, 8292. doi: 10.1039/C8OB01865K(56) Franz, M.; Stalling, T.; Steinert, H.; Martens, J. Org. Biomol. Chem. 2018, 16, 8292. doi: 10.1039/C8OB01865K
57. [57]
  (57) Zhang, Q.; Yuan, H.-Y.; Lin, X.-T.; Fukaya, N.; Fujitani, T.; Sato, K.; Choi, J.-C. Green Chem. 2020, 22, 4231. doi: 10.1039/D0GC01402H(57) Zhang, Q.; Yuan, H.-Y.; Lin, X.-T.; Fukaya, N.; Fujitani, T.; Sato, K.; Choi, J.-C. Green Chem. 2020, 22, 4231. doi: 10.1039/D0GC01402H
58. [58]
  (58) Sharma, S.; Singh, A. K.; Singh, D.; Kim, D. Green Chem. 2015, 17, 1404. doi: 10.1039/C4GC02089H(58) Sharma, S.; Singh, A. K.; Singh, D.; Kim, D. Green Chem. 2015, 17, 1404. doi: 10.1039/C4GC02089H
59. [59]
  (59) Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem. Int. Ed. 2016, 55, 10022. doi: 10.1002/anie.201603352(59) Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem. Int. Ed. 2016, 55, 10022. doi: 10.1002/anie.201603352
60. [60]
  (60) Xiong, W.; Qi, C.; Guo, T.; Zhang, M.; Chen, K.; Jiang, H. Green Chem. 2017, 19, 1642. doi: 10.1039/C6GC03465A(60) Xiong, W.; Qi, C.; Guo, T.; Zhang, M.; Chen, K.; Jiang, H. Green Chem. 2017, 19, 1642. doi: 10.1039/C6GC03465A
61. [61]
  (61) Bernoud, E.; Company, A.; Ribas, X. J. Organometal. Chem. 2017, 845, 44. doi: 10.1016/j.jorganchem.2017.02.004(61) Bernoud, E.; Company, A.; Ribas, X. J. Organometal. Chem. 2017, 845, 44. doi: 10.1016/j.jorganchem.2017.02.004
62. [62]
  (62) Luo, X.; Song, X.; Xiong, W.; Li, J.; Li, M.; Zhu, Z.; Wei, S.; Chan, A. S. C.; Zou, Y. Org. Lett. 2019, 21, 2013. doi: 10.1021/acs.orglett.9b00122(62) Luo, X.; Song, X.; Xiong, W.; Li, J.; Li, M.; Zhu, Z.; Wei, S.; Chan, A. S. C.; Zou, Y. Org. Lett. 2019, 21, 2013. doi: 10.1021/acs.orglett.9b00122
63. [63]
  (63) Wang, L.; Qi, C.; Cheng, R.; Liu, H.; Xiong, W.; Jiang, H. Org. Lett. 2019, 21, 7386. doi: 10.1021/acs.orglett.9b02698(63) Wang, L.; Qi, C.; Cheng, R.; Liu, H.; Xiong, W.; Jiang, H. Org. Lett. 2019, 21, 7386. doi: 10.1021/acs.orglett.9b02698
64. [64]
  (64) Ran, C.-K.; Huang, H.; Li, X.-H.; Wang, W.; Ye, J.-H.; Yan, S.-S.; Wang, B.-Q.; Feng, C.; Yu, D.-G. Chin. J. Chem. 2020, 38, 69. doi: 10.1002/cjoc.201900384(64) Ran, C.-K.; Huang, H.; Li, X.-H.; Wang, W.; Ye, J.-H.; Yan, S.-S.; Wang, B.-Q.; Feng, C.; Yu, D.-G. Chin. J. Chem. 2020, 38, 69. doi: 10.1002/cjoc.201900384
65. [65]
  (65) Wang, L.; Wang, P.; Guo, T.; Xiong, W.; Kang, B.; Qi, C.; Luo, G.; Luo, Y.; Jiang, H. Org. Chem. Front. 2021, 8, 1851. doi: 10.1039/D0QO01607A(65) Wang, L.; Wang, P.; Guo, T.; Xiong, W.; Kang, B.; Qi, C.; Luo, G.; Luo, Y.; Jiang, H. Org. Chem. Front. 2021, 8, 1851. doi: 10.1039/D0QO01607A
66. [66]
  (66) Li, S.; Ye, J.; Yuan, W.; Ma, S. Tetrahedron 2013, 69, 10450. doi: 10.1016/j.tet.2013.09.087(66) Li, S.; Ye, J.; Yuan, W.; Ma, S. Tetrahedron 2013, 69, 10450. doi: 10.1016/j.tet.2013.09.087
67. [67]
  (67) Cai, J.; Zhang, M.; Zhao, X. Eur. J. Org. Chem. 2015, 2015, 5925. doi: 10.1002/ejoc.201500769(67) Cai, J.; Zhang, M.; Zhao, X. Eur. J. Org. Chem. 2015, 2015, 5925. doi: 10.1002/ejoc.201500769
68. [68]
  (68) García-Domínguez, P.; Fehr, L.; Rusconi, G.; Nevado, C. Chem. Sci. 2016, 7, 3914. doi: 10.1039/C6SC00419A(68) García-Domínguez, P.; Fehr, L.; Rusconi, G.; Nevado, C. Chem. Sci. 2016, 7, 3914. doi: 10.1039/C6SC00419A
69. [69]
  (69) Xiong, W.; Yan, D.; Qi, C.; Jiang, H. Org. Lett. 2018, 20, 672. doi: 10.1021/acs.orglett.7b03808(69) Xiong, W.; Yan, D.; Qi, C.; Jiang, H. Org. Lett. 2018, 20, 672. doi: 10.1021/acs.orglett.7b03808
70. [70]
  (70) Zhou, C.; Dong, Y.; Yu, J.-T.; Sun, S.; Cheng, J. Chem. Commun. 2019, 55, 13685. doi: 10.1039/C9CC07027C(70) Zhou, C.; Dong, Y.; Yu, J.-T.; Sun, S.; Cheng, J. Chem. Commun. 2019, 55, 13685. doi: 10.1039/C9CC07027C
71. [71]
  (71) Xiong, W.; Cheng, R.; Wu, B.; Wu, W.; Qi, C.; Jiang, H. Sci. China Chem. 2020, 63, 331. doi: 10.1007/s11426-019-9679-6(71) Xiong, W.; Cheng, R.; Wu, B.; Wu, W.; Qi, C.; Jiang, H. Sci. China Chem. 2020, 63, 331. doi: 10.1007/s11426-019-9679-6
72. [72]
  (72) Song, Q.-W.; Zhou, Z.-H.; Yin, H.; He, L.-N. ChemSusChem 2015, 8, 3967. doi: 10.1002/cssc.201501176(72) Song, Q.-W.; Zhou, Z.-H.; Yin, H.; He, L.-N. ChemSusChem 2015, 8, 3967. doi: 10.1002/cssc.201501176
73. [73]
  (73) Sekine, K.; Kobayashi, R.; Yamada, T. Chem. Lett. 2015, 44, 1407. doi: 10.1246/cl.150584(73) Sekine, K.; Kobayashi, R.; Yamada, T. Chem. Lett. 2015, 44, 1407. doi: 10.1246/cl.150584
74. [74]
  (74) Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588. doi: 10.1021/acscatal.7b03370(74) Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588. doi: 10.1021/acscatal.7b03370
75. [75]
  (75) Qi, C.; Yan, D.; Xiong, W.; Jiang, H. Chin. J. Chem. 2018, 36, 399. doi: 10.1002/cjoc.201700808(75) Qi, C.; Yan, D.; Xiong, W.; Jiang, H. Chin. J. Chem. 2018, 36, 399. doi: 10.1002/cjoc.201700808
76. [76]
  (76) Qi, C.; Yan, D.; Xiong, W.; Jiang, H. J. CO₂ Util. 2018, 24, 120. doi: 10.1016/j.jcou.2017.12.013(76) Qi, C.; Yan, D.; Xiong, W.; Jiang, H. J. CO₂ Util. 2018, 24, 120. doi: 10.1016/j.jcou.2017.12.013
77. [77]
  (77) Zhang, M.; Zhao, X.; Zheng, S. Chem. Commun. 2014, 50, 4455. doi: 10.1039/C4CC00413B(77) Zhang, M.; Zhao, X.; Zheng, S. Chem. Commun. 2014, 50, 4455. doi: 10.1039/C4CC00413B
78. [78]
  (78) Watile, R.A.; Bhanage, B.M. RSC Adv. 2014, 4, 23022. doi: 10.1039/C4RA03836C(78) Watile, R.A.; Bhanage, B.M. RSC Adv. 2014, 4, 23022. doi: 10.1039/C4RA03836C
79. [79]
  (79) Shang, J.; Guo, X.; Li, Z.; Deng, Y. Green Chem. 2016, 18, 3082. doi: 10.1039/C5GC02772A(79) Shang, J.; Guo, X.; Li, Z.; Deng, Y. Green Chem. 2016, 18, 3082. doi: 10.1039/C5GC02772A
80. [80]
  (80) Jiang, H.; Zhang, H.; Xiong, W.; Qi, C.; Wu, W.; Wang, L.; Cheng, R. Org. Lett. 2019, 21, 1125. doi: 10.1021/acs.orglett.9b00072(80) Jiang, H.; Zhang, H.; Xiong, W.; Qi, C.; Wu, W.; Wang, L.; Cheng, R. Org. Lett. 2019, 21, 1125. doi: 10.1021/acs.orglett.9b00072
81. [81]
  (81) Wang, J.; Quian, P.; Hu, K.; Zha, Z.; Wang, Z. ChemElectroChem 2019, 6, 4292. doi: 10.1002/celc.201801724(81) Wang, J.; Quian, P.; Hu, K.; Zha, Z.; Wang, Z. ChemElectroChem 2019, 6, 4292. doi: 10.1002/celc.201801724
82. [82]
  (82) Xiong, T.-K.; Zhou, X.-Q.; Zhang, M.; Tang, H.-T.; Pan, Y.-M.; Liang, Y. Green Chem. 2021, 23, 4328. doi: 10.1039/D1GC00949D(82) Xiong, T.-K.; Zhou, X.-Q.; Zhang, M.; Tang, H.-T.; Pan, Y.-M.; Liang, Y. Green Chem. 2021, 23, 4328. doi: 10.1039/D1GC00949D
83. [83]
  (83) Fu, Z. Y.; Yang, Q.; Liu, Z.; Chen, F.; Yao, F. B.; Xie, T.; Wang, D. B.; Li, J.; Li, X. M.; Zeng, G. M.; et al. J. CO₂ Util. 2019, 34, 63. doi: 10.1016/j.jcou.2019.05.032(83) Fu, Z. Y.; Yang, Q.; Liu, Z.; Chen, F.; Yao, F. B.; Xie, T.; Wang, D. B.; Li, J.; Li, X. M.; Zeng, G. M.; et al. J. CO₂ Util. 2019, 34, 63. doi: 10.1016/j.jcou.2019.05.032
84. [84]
  (84) Wang, C. L.; Sun, Z. X.; Zheng, Y.; Hu, Y. H. J. Mater. Chem. A 2019, 7, 865. doi: 10.1039/c8ta09865d(84) Wang, C. L.; Sun, Z. X.; Zheng, Y.; Hu, Y. H. J. Mater. Chem. A 2019, 7, 865. doi: 10.1039/c8ta09865d
85. [85]
  (85) Schwalbe, M.; Huang, H.; Li, G. H. ChemPhotoChem 2022, 6, e20210021. doi: 10.1002/cptc.202100217(85) Schwalbe, M.; Huang, H.; Li, G. H. ChemPhotoChem 2022, 6, e20210021. doi: 10.1002/cptc.202100217
86. [86]
  (86) Huang, W.; Lin, J. Y.; Deng, F.; Zhong, H. Asian J. Org. Chem. 2022, 11, e202200220. doi: 10.1002/ajoc.202200220(86) Huang, W.; Lin, J. Y.; Deng, F.; Zhong, H. Asian J. Org. Chem. 2022, 11, e202200220. doi: 10.1002/ajoc.202200220
87. [87]
  (87) Qiu, L.-Q.; Yao, X. Y.; Zhang, Y.-K.; Li, H.-R.; He, L.-N. J. Org. Chem. 2023, 88, 4942. doi: 10.1021/acs.joc.2c02179(87) Qiu, L.-Q.; Yao, X. Y.; Zhang, Y.-K.; Li, H.-R.; He, L.-N. J. Org. Chem. 2023, 88, 4942. doi: 10.1021/acs.joc.2c02179
88. [88]
  (88) Wang, M.-Y.; Cao, Y.; Liu, X.; Wang, N.; He, L.-N.; Li, S.-H.; Green Chem. 2017, 19, 1240. doi: 10.1039/C6GC03200A(88) Wang, M.-Y.; Cao, Y.; Liu, X.; Wang, N.; He, L.-N.; Li, S.-H.; Green Chem. 2017, 19, 1240. doi: 10.1039/C6GC03200A
89. [89]
  (89) Yin, Z.-B.; Ye, J.-H.; Zhou, W.-J.; Zhang, Y.-H.; Ding, L.; Gui, Y.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Org. Lett. 2018, 20, 190. doi: 10.1021/acs.orglett.7b03551(89) Yin, Z.-B.; Ye, J.-H.; Zhou, W.-J.; Zhang, Y.-H.; Ding, L.; Gui, Y.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Org. Lett. 2018, 20, 190. doi: 10.1021/acs.orglett.7b03551
90. [90]
  (90) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G. Org. Lett. 2018, 20, 3049. doi: 10.1021/acs.orglett.8b01079(90) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G. Org. Lett. 2018, 20, 3049. doi: 10.1021/acs.orglett.8b01079
91. [91]
  (91) Sun, S.; Zhou, C.; Yu, J.-T.; Cheng, J. Org. Lett. 2019, 21, 6579. doi: 10.1021/acs.orglett.9b02700(91) Sun, S.; Zhou, C.; Yu, J.-T.; Cheng, J. Org. Lett. 2019, 21, 6579. doi: 10.1021/acs.orglett.9b02700
92. [92]
  (92) Cheng, R.; Qi, C.; Wang, L.; Xiong, W.; Liu, H.; Jiang, H. Green Chem. 2020, 22, 4890. doi: 10.1039/D0GC00910E(92) Cheng, R.; Qi, C.; Wang, L.; Xiong, W.; Liu, H.; Jiang, H. Green Chem. 2020, 22, 4890. doi: 10.1039/D0GC00910E
93. [93]
  (93) Wang, L.; Shi, F.; Qi, C.; Xu, W.; Xiong, W.; Kang, B.; Jiang, H. Chem. Sci. 2021, 12, 11821. doi: 10.1039/D1SC03366B(93) Wang, L.; Shi, F.; Qi, C.; Xu, W.; Xiong, W.; Kang, B.; Jiang, H. Chem. Sci. 2021, 12, 11821. doi: 10.1039/D1SC03366B
94. [94]
  (94) Guo, Y. H.; Wei, L.; Wen, Z. L.; Jiang, H.; Qi, C. Chem. Commun. 2023, 59, 764. doi: 10.1039/D2CC06033G(94) Guo, Y. H.; Wei, L.; Wen, Z. L.; Jiang, H.; Qi, C. Chem. Commun. 2023, 59, 764. doi: 10.1039/D2CC06033G
95. [95]
  (95) Sahari, A.; Puumi, J.; Mannisto, J. K.; Repo, T. J. Org. Chem. 2023, 88, 3822. doi: 10.1021/acs.joc.3c00023(95) Sahari, A.; Puumi, J.; Mannisto, J. K.; Repo, T. J. Org. Chem. 2023, 88, 3822. doi: 10.1021/acs.joc.3c00023

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沈阳化工大学材料科学与工程学院沈阳 110142

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通讯作者: 戚朝荣,Email:crqi@scut.edu.cn; 江焕峰,Email:jianghf@scut.edu.cn

English

Recent Progress on Conversion of Carbon Dioxide into Carbamates

Corresponding author: Chaorong Qi, ; Huanfeng Jiang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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中国化学会秘书处

二氧化碳转化为氨基甲酸酯的研究进展

通讯作者: 戚朝荣,Email:crqi@scut.edu.cn; 江焕峰,Email:jianghf@scut.edu.cn

English

Recent Progress on Conversion of Carbon Dioxide into Carbamates

Corresponding author: Chaorong Qi, ; Huanfeng Jiang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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