Citation: Jingjing Li, Sheng Zhang, Kun Xu. Recent advances towards electrochemical transformations of α-keto acids[J]. Chinese Chemical Letters, ;2021, 32(9): 2729-2735. doi: 10.1016/j.cclet.2021.03.027 shu

Recent advances towards electrochemical transformations of α-keto acids

Jingjing Li ^{a, b} ,
Sheng Zhang ^{c, *,} ,
Kun Xu ^{b, *,}

a.
Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
b.
Faculty of Environment and Life, Beijing University of Technology, Beijing 100024, China
c.
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, China

shengzhang@nynu.edu.cn

kunxu@bjut.edu.cn

Received Date: 22 January 2021
Revised Date: 8 March 2021
Accepted Date: 11 March 2021
Available Online: 13 March 2021

Figures(22)

As a kind of environmentally benign reagents, α-keto acids have been extensively employed as key starting materials in organic synthesis. Organic electrosynthesis has the advantages of reducing byproduct generation, improving the cost-efficiency of synthetic processes, and accessing reactive intermediates under mild conditions. Inspired by the merits of organic electrosynthesis, α-keto acids have shown many synthetic applications in electrochemical acylation, cyclization, and reductive amination reactions with improved efficiencies and selectivities. This review covers the recent breakthroughs achieved in the electrochemical transformations of α-keto acids, aimed at highlighting these electrochemical reactions' features and mechanistic rationalisations. Meanwhile, the practicalities and limitations of these transformations are also presented where possible.
- Electrosynthesis,
- Electrooxidation,
- Acylation,
- α-Keto acids,
- Decarboxylation
1. [1]
  J. Kay, P.D.J. Weitzman, Biochemical Society Symposia, Vol. 54, The Biochemical Society, London, 1987.
2. [2]
  D. Voet, J.G. Voet, Biochemistry, 3rd ed., John Wiley & Sons, New York, 2004
3. [3]
  L.J. Gooßen, F. Rudolphi, C. Oppel, N. Rodrguez, Angew. Chem. Int. Ed. 47 (2008) 3043-3045 doi: 10.1002/anie.200705127
4. [4]
  Y. Wei, P. Hu, M. Zhang, W. Su, Chem. Rev. 117 (2017) 8864-8907 doi: 10.1021/acs.chemrev.6b00516
5. [5]
  F. Penteado, E.F. Lopes, D. Alves, et al., Chem. Rev. 119 (2019) 7113-7278 doi: 10.1021/acs.chemrev.8b00782
6. [6]
  S. Tang, Y.C. Liu, A.W. Lei, Chem 4 (2018) 27-45 doi: 10.1016/j.chempr.2017.10.001
7. [7]
  Y.Y. Jiang, K. Xu, C.C. Zeng, Chem. Rev. 118 (2018) 4485-4540 doi: 10.1021/acs.chemrev.7b00271
8. [8]
  L. Ackermann, Acc. Chem. Res. 53 (2020) 84-104 doi: 10.1021/acs.accounts.9b00510
9. [9]
  P. Xiong, H.C. Xu, Acc. Chem. Res. 52 (2019) 3339-3350 doi: 10.1021/acs.accounts.9b00472
10. [10]
  Z.H. Ye, F.Z. Zhang, Chin. J. Chem. 37 (2019) 513-528 doi: 10.1002/cjoc.201900049
11. [11]
  K.J. Jiao, Y.K. Xing, Q.L. Yang, H. Qiu, T.S. Mei, Acc. Chem. Res. 53 (2020) 300-310 doi: 10.1021/acs.accounts.9b00603
12. [12]
  J. Liu, L. Lu, D. Wood, S. Lin, ACS Cent. Sci. 6 (2020) 1317-1340 doi: 10.1021/acscentsci.0c00549
13. [13]
  J. Zhong, Y. Yu, D. Zhang, K.Y. Ye, Chin. Chem. Lett. 32 (2021) 963-972. doi: 10.1016/j.cclet.2020.08.011
14. [14]
  T.J. DeLano, S.E. Reisman, ACS Catal. 9 (2019) 6751-6754 doi: 10.1021/acscatal.9b01785
15. [15]
  X. Liu, R. Liu, J. Qiu, X. Cheng, G. Li, Angew. Chem. Int. Ed. 59 (2020) 13962-13967 doi: 10.1002/anie.202005765
16. [16]
  P. Xu, P.Y. Chen, H.C. Xu, Angew. Chem. Int. Ed. 59 (2020) 14275-14280 doi: 10.1002/anie.202005724
17. [17]
  F. Wang, S.S. Stahl, Angew. Chem. Int. Ed. 58 (2019) 6385-6390 doi: 10.1002/anie.201813960
18. [18]
  L. Capaldo, L.L. Quadri, D. Ravelli, Angew. Chem. Int. Ed. 58 (2019) 17508-17510 doi: 10.1002/anie.201910348
19. [19]
  Z. Ye, Y. Wu, N. Chen, et al., Nat. Comm. 11 (2020) 3628 doi: 10.1038/s41467-020-17389-w
20. [20]
  L. Niu, C. Jiang, Y. Liang, et al., J. Am. Chem. Soc. 142 (2020) 17693-17702 doi: 10.1021/jacs.0c08437
21. [21]
  S. Zhang, L.J. Li, J.J. Zhang, et al., Chem. Sci. 10 (2019) 3181-3185 doi: 10.1039/C9SC00100J
22. [22]
  H. Wang, J.X. Shi, J. Tan, et al., Org. Lett. 21 (2019) 9430-9433 doi: 10.1021/acs.orglett.9b03641
23. [23]
  M.X. He, Z.Y. Mo, Z.Q. Wang, et al., Org. Lett. 22 (2020) 724-728 doi: 10.1021/acs.orglett.9b04549
24. [24]
  J. Zhang, H. Wang, Y. Chen, et al., Chin. Chem. Lett. 31 (2020) 1576-1579 doi: 10.1016/j.cclet.2019.11.037
25. [25]
  S. Zhang, L. Li, J. Shi, et al., Angew. Chem. Int. Ed. 60 (2021) 7275-7282. doi: 10.1002/anie.202015230
26. [26]
  J. Tauber, D. Imbri, T. Opatz, Molecules 19 (2014) 16190-16222 doi: 10.3390/molecules191016190
27. [27]
  W. Xiao, J. Wu, Chin. Chem. Lett. 31 (2020) 3083-3094 doi: 10.1016/j.cclet.2020.07.035
28. [28]
  L. Liu, P. Jiang, Y. Liu, H. Du, J. Tan, Org. Chem. Front. 7 (2020) 2278-2283 doi: 10.1039/D0QO00507J
29. [29]
  S. Peng, Y.X. Song, J.Y. He, et al., Chin. Chem. Lett. 30 (2019) 2287-2290 doi: 10.1016/j.cclet.2019.08.002
30. [30]
  L. Désaubry, J.J. Bourguignon, Tetrahedron Lett. 36 (1995) 7875-7876 doi: 10.1016/0040-4039(95)01647-Z
31. [31]
  F. Minisci, F. Recupero, A. Cecchetto, et al., Org. Process Res. Dev. 8 (2004) 163-168 doi: 10.1021/op034137w
32. [32]
  Q.Q. Wang, K. Xu, Y.Y. Jiang, et al., Org. Lett. 19 (2017) 5517-5520 doi: 10.1021/acs.orglett.7b02589
33. [33]
  H. Ding, K. Xu, C.C. Zeng, J. Catal. 381 (2020) 38-43 doi: 10.1016/j.jcat.2019.10.030
34. [34]
  B. Stanovnik, J. Svete, Chem. Rev. 104 (2004) 2433-2480 doi: 10.1021/cr020093y
35. [35]
  G. Negri, C. Kascheres, A.J. Kascheres, Heterocycl. Chem. 41 (2004) 413-491 doi: 10.1002/jhet.5570410318
36. [36]
  X. Kong, Y. Liu, L. Lin, Q. Chen, B. Xu, Green Chem. 21 (2019) 3796-3801 doi: 10.1039/C9GC01098J
37. [37]
  Y. Ning, X.F. Zhao, Y.B. Wu, X. Bi, Org. Lett. 19 (2017) 6240-6243 doi: 10.1021/acs.orglett.7b03204
38. [38]
  M. Hosseini-Sarvari, H. Sharghi, J. Org. Chem. 71 (2006) 652-6654
39. [39]
  J. Y. Quek, T. P. Davis, A. B. Lowe, Chem. Soc. Rev. 42 (2013) 7326-7334 doi: 10.1039/c3cs60065c
40. [40]
  R. Hett, Q.K. Fang, Y. Gao, S.A. Wald, C.H. Senanayake, Org. Process Res. Dev. 2 (1998) 96-99 doi: 10.1021/op970116o
41. [41]
  G. Ma, M. Zancanella, Y. Oyola, et al., Org. Lett. 8 (2006) 4497-4500 doi: 10.1021/ol061651o
42. [42]
  D.Z. Lin, J.M. Huang, Org. Lett. 20 (2018) 2112-2115 doi: 10.1021/acs.orglett.8b00698
43. [43]
  Y. Bansal, O. Silakari, Bioorg. Med. Chem. 20 (2012) 6208-6236 doi: 10.1016/j.bmc.2012.09.013
44. [44]
  P. Singla, V. Luxami, K. Paul, RSC Adv. 4 (2014) 12422-12440 doi: 10.1039/c3ra46304d
45. [45]
  H.B. Wang, J.M. Huang, Adv. Synth. Catal. 358 (2016) 1975-1981 doi: 10.1002/adsc.201501167
46. [46]
  F.B. Song, L.J. Gooßen, Adv. Synth. Catal. 353 (2011) 337-342 doi: 10.1002/adsc.201000798
47. [47]
  L.H. Chan, R.H. Lee, C.F. Hsieh, H.C. Yeh, C.T. Chen, J. Am. Chem. Soc. 124 (2002) 6469-6479 doi: 10.1021/ja0255150
48. [48]
  S. Valente, D. Trisciuoglio, T. De Luca, et al., J. Med. Chem. 57 (2014) 6259–6265 doi: 10.1021/jm500303u
49. [49]
  F. Lu, F. Gong, L. Li, et al., Eur. J. Org. 2020 (2020) 3257-3260 doi: 10.1002/ejoc.202000311
50. [50]
  S.B. Mhaske, N.P. Argade, Tetrahedron 62 (2006) 9787-9826 doi: 10.1016/j.tet.2006.07.098
51. [51]
  I. Khan, A. Ibrar, N. Abbas, A. Saeed, Eur. J. Med. Chem. 76 (2014) 193-244 doi: 10.1016/j.ejmech.2014.02.005
52. [52]
  P.P. Kung, M.D. Casper, K.L. Cook, et al., J. Med. Chem. 42 (1999) 4705-4713 doi: 10.1021/jm9903500
53. [53]
  Q. Tian, J. Zhang, L. Xu, Y. Wei, Molecular Catal. 500 (2021) 111345 doi: 10.1016/j.mcat.2020.111345
54. [54]
  D.H. Baker, Amino Acids 37 (2009) 29-41 doi: 10.1007/s00726-008-0198-3
55. [55]
  G. Wu, Amino Acids 37 (2009) 1-17
56. [56]
  H. Groger, Chem. Rev. 103 (2003) 2795-2828 doi: 10.1021/cr020038p
57. [57]
  E.A. Jeffery, O. Johansen, A. Meisters, Aust. J. Chem. 31 (1978) 73-78 doi: 10.1071/CH9780073
58. [58]
  E.A. Jeffery, O. Johansen, A. Meisters, Aust. J. Chem. 31 (1978) 79-84 doi: 10.1071/CH9780079
59. [59]
  T. Fukushima, M. Yamauchi, Chem. Commun. 55 (2019) 14721-14724 doi: 10.1039/C9CC07208J
1. [1]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
2. [2]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
3. [3]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
4. [4]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
5. [5]
  Wen-Bo Wei , Qi-Long Zhu . Electrosynthesis of hydroxylamine from earth-abundant small molecules. Chinese Journal of Structural Chemistry, 2025, 44(1): 100383-100383. doi: 10.1016/j.cjsc.2024.100383
6. [6]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
7. [7]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
8. [8]
  Lili Wang , Ya Yan , Rulin Li , Xujie Han , Jiahui Li , Ting Ran , Jialu Li , Baichuan Xiong , Xiaorong Song , Zhaohui Yin , Hong Wang , Qingjun Zhu , Bowen Cheng , Zhen Yin . Interface engineering of 2D NiFe LDH/NiFeS heterostructure for highly efficient 5-hydroxymethylfurfural electrooxidation. Chinese Chemical Letters, 2024, 35(9): 110011-. doi: 10.1016/j.cclet.2024.110011
9. [9]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
10. [10]
  Ke Wang , Jia Wu , Shuyi Zheng , Shibin Yin . NiCo Alloy Nanoparticles Anchored on Mesoporous Mo2N Nanosheets as Efficient Catalysts for 5-Hydroxymethylfurfural Electrooxidation and Hydrogen Generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100104-100104. doi: 10.1016/j.cjsc.2023.100104
11. [11]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
12. [12]
  Kaili Wang , Pengcheng Liu , Mingzhe Wang , Tianran Wei , Jitao Lu , Xingling Zhao , Zaiyong Jiang , Zhimin Yuan , Xijun Liu , Jia He . Modulating d-d orbitals coupling in PtPdCu medium-entropy alloy aerogels to boost pH-general methanol electrooxidation performance. Chinese Chemical Letters, 2025, 36(4): 110532-. doi: 10.1016/j.cclet.2024.110532
13. [13]
  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
14. [14]
  Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P₄S₁₀ and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513
15. [15]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
16. [16]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
17. [17]
  Hongmei Yu , Baoxi Zhang , Meiju Liu , Cheng Xing , Guorong He , Li Zhang , Ningbo Gong , Yang Lu , Guanhua Du . Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers. Chinese Chemical Letters, 2024, 35(5): 109032-. doi: 10.1016/j.cclet.2023.109032
18. [18]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
19. [19]
  Yanjing Li , Jiayin Li , Yuqi Chang , Yunfeng Lin , Lei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414
20. [20]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665

Get Citation

PDF

XML

Metrics

PDF Downloads(22)
Abstract views(829)
HTML views(54)

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