Citation: Han Li-Hua, Li Jing-Yuan, Song Qing-Wen, Zhang Kan, Zhang Qian-Xia, Sun Xiao-Fang, Liu Ping. Thermodynamic favorable CO₂ conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method[J]. Chinese Chemical Letters, ;2020, 31(2): 341-344. doi: 10.1016/j.cclet.2019.06.030 shu

Thermodynamic favorable CO₂ conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method

State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China

songqingwen@sxicc.ac.cn

pingliu@sxicc.ac.cn

Received Date: 29 April 2019
Revised Date: 10 June 2019
Accepted Date: 18 June 2019
Available Online: 18 June 2019

Figures(5)

Organocatalysis represents a promising field in chemical fixation of CO₂. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO₂. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side reactions under the metal-free conditions.
- Carbon dioxide utilization,
- Cascade reaction,
- Chemicals,
- Metal-free catalysis,
- Synthetic methods
1. [1]
  M. He, Y. Sun, B. Han, Angew. Chem. Int. Ed. 52 (2013) 9620-9633. doi: 10.1002/anie.201209384
2. [2]
  M. Aresta, A. Dibenedetto, A. Angelini, Chem. Rev. 114 (2014) 1709-1742. doi: 10.1021/cr4002758
3. [3]
  M. Cokoja, C. Bruckmeier, B. Rieger, W.A. Herrmann, F.E. Kühn, Angew. Chem. Int. Ed. 50 (2011) 8510-8537. doi: 10.1002/anie.201102010
4. [4]
  Q. Liu, L. Wu, R. Jackstell, M. Beller, Nat. Commun. 6 (2015) 5933-5948. doi: 10.1038/ncomms6933
5. [5]
  A. Otto, T. Grube, S. Schiebahn, D. Stolten, Energy Environ. Sci. 8 (2015) 3283-3297. doi: 10.1039/C5EE02591E
6. [6]
  B. Yu, L.N. He, ChemSusChem 8 (2015) 52-62. doi: 10.1002/cssc.201402837
7. [7]
  T.E. Muller, W. Leitner, Beilstein J. Org. Chem. 11 (2015) 675-677. doi: 10.3762/bjoc.11.76
8. [8]
  X.B. Lu, D.J. Darensbourg, Chem. Soc. Rev. 41 (2012) 1462-1484. doi: 10.1039/C1CS15142H
9. [9]
  K. Huang, C.L. Sun, Z.J. Shi, Chem. Soc. Rev. 40 (2011) 2435-2452. doi: 10.1039/c0cs00129e
10. [10]
  M. Cokoja, M.E. Wilhelm, M.H. Anthofer, W.A. Herrmann, F.E. Kuhn, ChemSusChem 8 (2015) 2436-2454. doi: 10.1002/cssc.201500161
11. [11]
  G. Fiorani, W. Guo, A.W. Kleij, Green Chem. 17 (2015) 1375-1389. doi: 10.1039/C4GC01959H
12. [12]
  Y. Kayaki, M. Yamamoto, T. Ikariya, Angew. Chem. Int. Ed. 48 (2009) 4194-4197. doi: 10.1002/anie.200901399
13. [13]
  A. Ueno, Y. Kayaki, T. Ikariya, Green Chem. 15 (2013) 425-430. doi: 10.1039/C2GC36414J
14. [14]
  K.I. Fujita, A. Fujii, J. Sato, S.Y. Onozawa, H. Yasuda, Tetrahedron Lett. 57 (2016) 1282-1284. doi: 10.1016/j.tetlet.2016.02.027
15. [15]
  O. Jacquet, C. Das Neves Gomes, M. Ephritikhine, T. Cantat, J. Am. Chem. Soc. 134 (2012) 2934-2937. doi: 10.1021/ja211527q
16. [16]
  Y.B. Wang, Y.M. Wang, W.Z. Zhang, X.B. Lu, J. Am. Chem. Soc. 135 (2013) 11996-12003. doi: 10.1021/ja405114e
17. [17]
  Y.B. Wang, D.S. Sun, H. Zhou, W.Z. Zhang, X.B. Lu, Green Chem. 17 (2015) 4009-4015. doi: 10.1039/C5GC00948K
18. [18]
  C.M. Mömming, E. Otten, G. Kehr, et al., Angew. Chem. Int. Ed. 48 (2009) 6643-6646. doi: 10.1002/anie.200901636
19. [19]
  T. Wang, D.W. Stephan, Chem. Eur. J. 20 (2014) 3036-3039. doi: 10.1002/chem.201304870
20. [20]
  A.E. Ashley, A.L. Thompson, D. O'Hare, Angew. Chem. Int. Ed. 48 (2009) 9839-9843. doi: 10.1002/anie.200905466
21. [21]
  N. von Wolff, G. Lefèvre, J.C. Berthet, P. Thuéry, T. Cantat, ACS Catal. 6 (2016) 4526-4535. doi: 10.1021/acscatal.6b00421
22. [22]
  Z. Xin, C. Lescot, S.D. Friis, K. Daasbjerg, T. Skrydstrup, Angew. Chem. Int. Ed. 54 (2015) 6862-6866. doi: 10.1002/anie.201500233
23. [23]
  X. Frogneux, E. Blondiaux, P. Thuéry, T. Cantat, ACS Catal. 5 (2015) 3983-3987. doi: 10.1021/acscatal.5b00734
24. [24]
  E. Blondiaux, J. Pouessel, T. Cantat, Angew. Chem. Int. Ed. 53 (2014) 12186-12190. doi: 10.1002/anie.201407357
25. [25]
  X.D. Lang, Y.C. Yu, Z.M. Li, L.N. He, J. CO₂. Util. 15 (2016) 115-122. doi: 10.1016/j.jcou.2016.03.002
26. [26]
  X. Gao, B. Yu, Z. Yang, et al., ACS Catal. 5 (2015) 6648-6652. doi: 10.1021/acscatal.5b01874
27. [27]
  M. Liu, L. Liang, X. Li, X. Gao, J. Sun, Green Chem. 18 (2016) 2851-2863. doi: 10.1039/C5GC02605A
28. [28]
  Y.B. Wang, D.S. Sun, H. Zhou, W.Z. Zhang, X.B. Lu, Green Chem. 16 (2014) 2266-2272. doi: 10.1039/C3GC42346H
29. [29]
  H. Zhou, G.X. Wang, W.Z. Zhang, X.B. Lu, ACS Catal. 5 (2015) 6773-6779. doi: 10.1021/acscatal.5b01409
30. [30]
  M.A. Courtemanche, M.A. Légaré, É. Rochette, F.G. Fontaine, Chem. Commun. (Camb.) 51 (2015) 6858-6861. doi: 10.1039/C5CC01282A
31. [31]
  Z.H. Zhou, Q.W. Song, L.N. He, ACS Omega 2 (2017) 337-345. doi: 10.1021/acsomega.6b00407
32. [32]
  J.Y. Li, L.H. Han, Q.C. Xu, et al., ACS Sustainable Chem. Eng. 7 (2019) 3378-3388. doi: 10.1021/acssuschemeng.8b05579
33. [33]
  X.D. Li, Y. Cao, R. Ma, L.N. He, J. CO₂. Util 25 (2018) 338-345. doi: 10.1016/j.jcou.2018.01.022
34. [34]
  Q.W. Song, Q.N. Zhao, J.Y. Li, K. Zhang, P. Liu, Synthesis 51 (2018) 739-746.
35. [35]
  J. Sun, W. Cheng, Z. Yang, et al., Green Chem. 16 (2014) 3071-3078. doi: 10.1039/c3gc41850b
36. [36]
  R. Nicholls, S. Kaufhold, B.N. Nguyen, Catal. Sci. Technol. 4 (2014) 3458-3462. doi: 10.1039/C4CY00480A
37. [37]
  Z.Z. Yang, Y.N. Zhao, L.N. He, J. Gao, Z.S. Yin, Green Chem. 14 (2012) 519-527. doi: 10.1039/c2gc16039k
38. [38]
  K. Chen, G. Shi, R. Dao, et al., Chem. Commun. (Camb.) 52 (2016) 7830-7833. doi: 10.1039/C6CC02853E
39. [39]
  N.D. Ca, B. Gabriele, G. Ruffolo, et al., Adv. Synth. Catal. 353 (2011) 133-146. doi: 10.1002/adsc.201000607
40. [40]
  M. Baidya, H. Mayr, Chem. Commun. (Camb.) (2008) 1792-1794.
41. [41]
  M. Hulla, S.M.A. Chamam, G. Laurenczy, S. Das, P.J. Dyson, Angew. Chem. 129 (2017) 10695-10699. doi: 10.1002/ange.201705438
42. [42]
  T. Mizuno, Y. Ishino, Tetrahedron 58 (2002) 3155-3158. doi: 10.1016/S0040-4020(02)00279-X
43. [43]
  P.G. Jessop, B. Subramaniam, Chem. Rev. 107 (2007) 2666-2694. doi: 10.1021/cr040199o
44. [44]
  C. Roosen, M. Ansorge-Schumacher, T. Mang, W. Leitner, L. Greiner, Green Chem. 9 (2007) 455-458. doi: 10.1039/b613345b
45. [45]
  E.R. Pérez, R.H.A. Santos, M.T.P. Gambardella, et al., J. Org. Chem. 69 (2004) 8005-8011. doi: 10.1021/jo049243q
1. [1]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
2. [2]
  Qiyan Wu , Qing Li . Topologically close-packed intermetallic alloy electrocatalysts for CO₂ reduction towards high value-added multi-carbon chemicals. Chinese Chemical Letters, 2025, 36(1): 110384-. doi: 10.1016/j.cclet.2024.110384
3. [3]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
4. [4]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
5. [5]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
6. [6]
  Jian Yang , Guang Yang , Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267
7. [7]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
8. [8]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
9. [9]
  Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
10. [10]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
11. [11]
  Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
12. [12]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
13. [13]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
14. [14]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
15. [15]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
16. [16]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
17. [17]
  Xue-Zhi Wang , Yi-Tong Liu , Chuang-Wei Zhou , Bei Wang , Dong Luo , Mo Xie , Meng-Ying Sun , Yong-Liang Huang , Jie Luo , Yan Wu , Shuixing Zhang , Xiao-Ping Zhou , Dan Li . Amplified circularly polarized luminescence of chiral metal-organic frameworks via post-synthetic installing pillars. Chinese Chemical Letters, 2024, 35(10): 109380-. doi: 10.1016/j.cclet.2023.109380
18. [18]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
19. [19]
  Wei-Jia Wang , Kaihong Chen . Molecular-based porous polymers with precise sites for photoreduction of carbon dioxide. Chinese Chemical Letters, 2025, 36(1): 109998-. doi: 10.1016/j.cclet.2024.109998
20. [20]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(978)
HTML views(68)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method

Metrics

通讯作者: 陈斌, bchen63@163.com

Thermodynamic favorable CO₂ conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method