Citation: Xiaofei Liu, He Wang, Li Tao, Weimin Ren, Xiaobing Lu, Wenzhen Zhang. Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide[J]. Acta Physico-Chimica Sinica, ;2024, 40(9): 230700. doi: 10.3866/PKU.WHXB202307008 shu

Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide

State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials, Dalian University of Technology, Dalian 116024, Liaoning Province, China

Corresponding author: Wenzhen Zhang, zhangwz@dlut.edu.cn
Received Date: 3 July 2023
Revised Date: 27 July 2023
Accepted Date: 27 July 2023

Fund Project: This work was supported by the National Natural Science Foundation of China (22278054, 21920102006) and the Fundamental Research Funds for the Central Universities, China (DUT22LAB609).

Carbon dioxide (CO₂) serves as a non-toxic, abundant, cheap, and renewable C1 feedstock in synthetic chemistry. The synthesis of high value-added fine chemicals, such as organic carboxylic acids, using CO₂, is always a focal point of research. Due to the thermodynamic stability and kinetic inertness of carbon dioxide, traditional carboxylation reactions utilizing CO₂ often require harsh reaction conditions. However, organic electrochemical synthesis, which employs electrons as clean reagents to drive the reaction and avoids additional chemical oxidants or reductants, has emerged as a safer, more economical, highly selective, sustainable, and environmentally friendly method for preparing fine chemicals. Electrocarboxylation, which leverages organic electrochemical synthesis to catalytically transform CO₂, provides a milder and more efficient route for CO₂ utilization. Among these approaches, electrocarboxylation of organic halides or pseudohalides containing C―X bonds with CO₂ has been extensively investigated as a means to access value-added carboxylic acids. Phosphates, known for their good leaving group properties, find extensive applications in organic synthesis. Under reductive conditions, the radical anion generated by benzyl phosphate easily dissociates into a benzyl radical and a phosphate anion. Hence, it can serve as an attractive substrate for participating in electrocarboxylation reactions. In this study, we report the highly efficient electrocarboxylation of benzylic phosphate and phosphinate derivatives using CO₂ as the carboxyl source. The constant current reaction took place in an undivided cell, employing glassy carbon as the cathode, and magnesium as the sacrificial anode, in a mixed solvent of DMF and THF. Additionally, this mild electrolysis can be carried out under nonsacrificial anode conditions, using cheap carbon felt electrode as both the nonsacrificial anode and cathode and N,N-diisopropylethylamine as an external reductant, therefore provided operationally simple and highly efficient synthetic method toward aryl acetic acids in moderate to good yield. The broad substrate scope, simple operation, facile scalability, and highly efficient transformation of phosphates into high value-added aryl acetic acids under mild conditions demonstrate the potential applicability of this reaction. To gain insight into the possible reaction mechanism, several control experiments were conducted. Isotope-labeling ¹³CO₂ experiment, cyclic voltammetry experiments, radical trapping reactions, and deuterium-labeling experiment indicated that cathodically generated benzylic radical and benzylic anion were key intermediates. Moreover, the single electron reduction of CO₂ to CO₂^•− might also occur during the reaction.
- Electrocarboxylation,
- Nonsacrificial anode reaction,
- Carbon dioxide,
- Phosphates,
- Aryl acetic acids
1. [1]
  (1) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933. doi: 10.1038/ncomms6933
2. [2]
  (2) Jacob, D.; Julien, R. L.; Dmitry, P. Z.; Ruben, M. Chem 2021, 7, 2927. doi: 10.1016/j.chempr.2021.10.016
3. [3]
  (3) Cai, S. F.; Li, H. R.; He, L. N. Green Chem. 2021, 23, 9334. doi: 10.1039/d1gc02783b
4. [4]
  (4) Wang, L.; Qi, C.; Xiong, W.; Jiang, H. Chin. J. Catal. 2022, 43, 1598. doi: 10.1016/s1872-2067(21)64029-9
5. [5]
  (5) Ye, J. H.; Ju, T.; Huang, H.; Liao, L. L.; Yu, D. G. Acc. Chem. Res. 2021, 54, 2518. doi: 10.1021/acs.accounts.1c00135
6. [6]
  (6) Yi, Y.; Xi, C. Chin. J. Catal. 2022, 43, 1652. doi: 10.1016/s1872-2067(21)63956-6
7. [7]
  (7) Blobaum, A. L.; Marnett, L. J. J. Biol. Chem. 2007, 282, 16379. doi: 10.1074/jbc.M609883200
8. [8]
  (8) Senboku, H.; Yoneda, K.; Hara, S. Tetrahedron Lett. 2015, 56, 6772. doi: 10.1016/j.tetlet.2015.10.068
9. [9]
  (9) Mita, T.; Higuchi, Y.; Sato, Y. Chem. Eur. J. 2015, 21, 16391. doi: 10.1002/chem.201503359
10. [10]
  (10) Shao, P.; Wang, S.; Chen, C.; Xi, C. Org. Lett. 2016, 18, 2050. doi: 10.1021/acs.orglett.6b00665
11. [11]
  (11) Leon, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221. doi: 10.1021/ja311045f
12. [12]
  (12) Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem. Int. Ed. 2016, 55, 5053. doi: 10.1002/anie.201600697
13. [13]
  (13) Liao, L. L.; Cao, G. M.; Ye, J. H.; Sun, G. Q.; Zhou, W. J.; Gui, Y. Y.; Yan, S. S.; Shen, G.; Yu, D. G. J. Am. Chem. Soc. 2018, 140, 17338. doi: 10.1021/jacs.8b08792
14. [14]
  (14) Ran, C. K.; Niu, Y. N.; Song, L.; Wei, M. K.; Cao, Y. F.; Luo, S. P.; Yu, Y. M.; Liao, L. L.; Yu, D. G. ACS Catal. 2022, 12, 18. doi: 10.1021/acscatal.1c04921
15. [15]
  (15) Jing, K.; Wei, M.-K.; Yan, S.-S.; Liao, L.-L.; Niu, Y.-N.; Luo, S.-P.; Yu, B.; Yu, D.-G. Chin. J. Catal. 2022, 43, 1667. doi: 10.1016/s1872-2067(21)63859-7
16. [16]
  (16) Yan, S. S.; Liu, S. H.; Chen, L.; Bo, Z. Y.; Jing, K.; Gao, T. Y.; Yu, B.; Lan, Y.; Luo, S. P.; Yu, D. G. Chem 2021, 7, 3099. doi: 10.1016/j.chempr.2021.08.004
17. [17]
  (17) Jin, Y.; Toriumi, N.; Iwasawa, N. ChemSusChem 2022, 15, e202200021. doi: 10.1002/cssc.202200021
18. [18]
  (18) Zhang, S.; Chen, W. Q.; Yu, A.; He, L. N. ChemCatChem 2015, 7, 3972. doi: 10.1002/cctc.201500724
19. [19]
  (19) Hang, W.; Li, D.; Zou, S.; Xi, C. J. Org. Chem. 2023, 88, 5007. doi: 10.1021/acs.joc.2c01840
20. [20]
  (20) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397
21. [21]
  (21) Yuan, Y.; Yang, J.; Lei, A. Chem. Soc. Rev. 2021, 50, 10058. doi: 10.1039/d1cs00150g
22. [22]
  (22) Jiao, K. J.; Xing, Y. K.; Yang, Q. L.; Qiu, H.; Mei, T. S. Acc. Chem. Res. 2020, 53, 300. doi: 10.1021/acs.accounts.9b00603
23. [23]
  (23) Rockl, J. L.; Pollok, D.; Franke, R.; Waldvogel, S. R. Acc. Chem. Res. 2020, 53, 45. doi: 10.1021/acs.accounts.9b00511
24. [24]
  (24) Siu, J. C.; Fu, N.; Lin, S. Acc. Chem. Res. 2020, 53, 547. doi: 10.1021/acs.accounts.9b00529
25. [25]
  (25) Zhu, C.; Ang, N. W. J.; Meyer, T. H.; Qiu, Y.; Ackermann, L. ACS Cent. Sci. 2021, 7, 415. doi: 10.1021/acscentsci.0c01532
26. [26]
  (26) Novaes, L. F. T.; Liu, J.; Shen, Y.; Lu, L.; Meinhardt, J. M.; Lin, S. Chem. Soc. Rev. 2021, 50, 7941. doi: 10.1039/d1cs00223f
27. [27]
  (27) Liu, Y.; Li, P.; Wang, Y.; Qiu, Y. Angew. Chem. Int. Ed. 2023, e202306679. doi: 10.1002/anie.202306679
28. [28]
  (28) Cheng, X.; Lei, A.; Mei, T.-S.; Xu, H.-C.; Xu, K.; Zeng, C. CCS Chem. 2022, 4, 1120. doi: 10.31635/ccschem.021.202101451
29. [29]
  (29) Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Res. 2020, 53, 72. doi: 10.1021/acs.accounts.9b00539
30. [30]
  (30) Chang, X.; Zhang, Q.; Guo, C. Angew. Chem. Int. Ed. 2020, 59, 12612. doi: 10.1002/anie.202000016
31. [31]
  (31) Senboku, H.; Katayama, A. Curr. Opin. Green Sustain. Chem. 2017, 3, 50. doi: 10.1016/j.cogsc.2016.10.003
32. [32]
  (32) Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19. doi: 10.1016/j.gresc.2021.01.009
33. [33]
  (33) Liu, X.-F.; Zhang, K.; Tao, L.; Lu, X.-B.; Zhang, W.-Z. Green Chem. Eng. 2022, 3, 125. doi: 10.1016/j.gce.2021.12.001
34. [34]
  (34) Zhang, K.; Liu, X. F.; Ren, W. M.; Lu, X. B.; Zhang, W. Z. Chem. Eur. J. 2023, 29, e202204073. doi: 10.1002/chem.202204073
35. [35]
  (35) Wang, S.; Feng, T.; Wang, Y.; Qiu, Y. Chem. Asian J. 2022, 17, e202200543. doi: 10.1002/asia.202200543
36. [36]
  (36) Wang, Y.; Zhao, Z.; Pan, D.; Wang, S.; Jia, K.; Ma, D.; Yang, G.; Xue, X. S.; Qiu, Y. Angew. Chem. Int. Ed. 2022, 61, e202210201. doi: 10.1002/anie.202210201
37. [37]
  (37) Sun, G. Q.; Zhang, W.; Liao, L. L.; Li, L.; Nie, Z. H.; Wu, J. G.; Zhang, Z.; Yu, D. G. Nat. Commun. 2021, 12, 7086. doi: 10.1038/s41467-021-27437-8
38. [38]
  (38) Tummanapalli, S.; Gulipalli, K. C.; Endoori, S.; Bodige, S.; Kumar Pommidi, A.; Medaboina, S.; Rejinthala, S.; Choppadandi, S.; Boya, R.; Kanuka, A.; et al. Tetrahedron Lett. 2022, 104, 154022. doi: 10.1016/j.tetlet.2022.154022
39. [39]
  (39) Corbin, N.; Junor, G. P.; Ton, T. N.; Baker, R. J.; Manthiram, K. J. Am. Chem. Soc. 2023, 145, 1740. doi: 10.1021/jacs.2c10561
40. [40]
  (40) Ang, N. W. J.; Oliveira, J. C. A.; Ackermann, L. Angew. Chem. Int. Ed. 2020, 59, 12842. doi: 10.1002/anie.202003218
41. [41]
  (41) Jiao, K. J.; Li, Z. M.; Xu, X. T.; Zhang, L. P.; Li, Y. Q.; Zhang, K.; Mei, T. S. Org. Chem. Front. 2018, 5, 2244. doi: 10.1039/c8qo00507a
42. [42]
  (42) Sun, G. Q.; Yu, P.; Zhang, W.; Zhang, W.; Wang, Y.; Liao, L. L.; Zhang, Z.; Li, L.; Lu, Z.; Yu, D. G.; et al. Nature 2023, 615, 67. doi: 10.1038/s41586-022-05667-0
43. [43]
  (43) Zhao, Z.; Liu, Y.; Wang, S.; Tang, S.; Ma, D.; Zhu, Z.; Guo, C.; Qiu, Y. Angew. Chem. Int. Ed. 2023, 62, e202214710. doi: 10.1002/anie.202214710
44. [44]
  (44) Rawat, V. K.; Hayashi, H.; Katsuyama, H.; Mangaonkar, S. R.; Mita, T. Org. Lett. 2023, 25, 4231. doi: 10.1021/acs.orglett.3c01033
45. [45]
  (45) Zhang, W.; Liao, L. L.; Li, L.; Liu, Y.; Dai, L. F.; Sun, G. Q.; Ran, C. K.; Ye, J. H.; Lan, Y.; Yu, D. G. Angew. Chem. Int. Ed. 2023, 62, e202301892. doi: 10.1002/anie.202301892
46. [46]
  (46) Sheta, A. M.; Alkayal, A.; Mashaly, M. A.; Said, S. B.; Elmorsy, S. S.; Malkov, A. V.; Buckley, B. R. Angew. Chem. Int. Ed. 2021, 60, 21832. doi: 10.1002/anie.202105490
47. [47]
  (47) Sheta, A. M.; Mashaly, M. A.; Said, S. B.; Elmorsy, S. S.; Malkov, A. V.; Buckley, B. R. Chem. Sci. 2020, 11, 9109. doi: 10.1039/d0sc03148h
48. [48]
  (48) Alkayal, A.; Tabas, V.; Montanaro, S.; Wright, I. A.; Malkov, A. V.; Buckley, B. R. J. Am. Chem. Soc. 2020, 142, 1780. doi: 10.1021/jacs.9b13305
49. [49]
  (49) Zhang, W.; Lin, S. J. Am. Chem. Soc. 2020, 142, 20661. doi: 10.1021/jacs.0c08532
50. [50]
  (50) Liao, L. L.; Wang, Z. H.; Cao, K. G.; Sun, G. Q.; Zhang, W.; Ran, C. K.; Li, Y.; Chen, L.; Yu, D. G. J. Am. Chem. Soc. 2022, 144, 2062. doi: 10.1021/jacs.1c12071
51. [51]
  (51) Zhao, B.; Pan, Z.; Pan, J.; Deng, H.; Bu, X.; Ma, M.; Xue, F. Green Chem. 2023, 25, 3095. doi: 10.1039/d2gc04636a
52. [52]
  (52) You, Y.; Kanna, W.; Takano, H.; Hayashi, H.; Maeda, S.; Mita, T. J. Am. Chem. Soc. 2022, 144, 3685. doi: 10.1021/jacs.1c13032
53. [53]
  (53) Wang, Y.; Tang, S.; Yang, G.; Wang, S.; Ma, D.; Qiu, Y. Angew. Chem. Int. Ed. 2022, e202207746. doi: 10.1002/anie.202207746
54. [54]
  (54) Scott J. H.; Mark D. E. J. Med. Chem. 2008, 51, 2328. doi: 10.1021/jm701260b
55. [55]
  (55) Pradere, U.; Garnier-Amblard, E. C.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Chem. Rev. 2014, 114, 9154. doi: 10.1021/cr5002035
56. [56]
  (56) Trost, B. M.; Czabaniuk, L. C. J. Am. Chem. Soc. 2012, 134, 5778. doi: 10.1021/ja301461p
57. [57]
  (57) He, Y.; Huang, L.; Xie, L.; Liu, P.; Wei, Q.; Mao, F.; Zhang, X.; Huang, J.; Chen, S.; Huang, C. J. Org. Chem. 2019, 84, 10088. doi: 10.1021/acs.joc.9b01278
58. [58]
  (58) Schwarz, K. J.; Yang, C.; Fyfe, J. W. B.; Snaddon, T. N. Angew. Chem. Int. Ed. 2018, 57, 12102. doi: 10.1002/anie.201806742
59. [59]
  (59) Liu, W.; Zheng, Y. Chin. J. Org. Chem. 2021, 41, 3344. doi: 10.6023/cjoc202100061
60. [60]
  (60) Wang, H.; Wang, Z.; Zhao, G.; Ramadoss, V.; Tian, L.; Wang, Y. Org. Lett. 2022, 24, 3668. doi: 10.1021/acs.orglett.2c01286
61. [61]
  (61) Zhang, K.; Liu, X. F.; Zhang, W. Z.; Ren, W. M.; Lu, X. B. Org. Lett. 2022, 24, 3565. doi: 10.1021/acs.orglett.2c01267
62. [62]
  (62) Zhang, K.; Ren, B. H.; Liu, X. F.; Wang, L. L.; Zhang, M.; Ren, W. M.; Lu, X. B.; Zhang, W. Z. Angew. Chem. Int. Ed. 2022, 61, e202207660. doi: 10.1002/anie.202207660
63. [63]
  (63) Liu, X. F.; Zhang, K.; Wang, L. L.; Wang, H.; Huang, J.; Zhang, X. T.; Lu, X. B.; Zhang, W. Z. J. Org. Chem. 2023, 88, 5212. doi: 10.1021/acs.joc.2c01816
64. [64]
  (64) Wang, L. L.; Liu, X. F.; Wang, H.; Tao, L.; Huang, J.; Ren, W. M.; Lu, X. B.; Zhang, W. Z. Synthesis 2023, 55, 2951. doi: 10.1055/s-0041-1738439
65. [65]
  (65) Deposition no. 2278317 (for 2t) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data_request/cif, accessed on Aug 2, 2023).
66. [66]
  (66) Chen, X. W.; Zhu, L.; Gui, Y. Y.; Jing, K.; Jiang, Y. X.; Bo, Z. Y.; Lan, Y.; Li, J.; Yu, D. G. J. Am. Chem. Soc. 2019, 141, 18825. doi: 10.1021/jacs.9b09721
67. [67]
  (67) Chen, X. W.; Yue, J. P.; Wang, K.; Gui, Y. Y.; Niu, Y. N.; Liu, J.; Ran, C. K.; Kong, W.; Zhou, W. J.; Yu, D. G. Angew. Chem. Int. Ed. 2021, 60, 14068. doi: 10.1002/anie.202102769
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