Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of α-Hydroxycarboxylic Acids from Various Aldehydes and Ketones by Direct Electrocarboxylation: A Facile, Efficient and Atom Economy Protocol
Corresponding Author(s) : Baljit Singh
Asian Journal of Chemistry,
Vol. 33 No. 4 (2021): Vol 33 Issue 4
Abstract
In present work, the formation of α-hydroxycarboxylic acids have been described from various aromatic aldehydes and ketones via direct electrocarboxylation method with 80-92% of yield without any side product and can be purified by simple recrystallization using sacrificial Mg anode and Pt cathode in an undivided cell, CO2 at (1 atm) was continuously bubbled in the cell throughout the reaction using tetrapropyl-ammonium chloride as a supporting electrolyte in acetonitrile. The synthesized compounds obtained in fair to excellent yield with a high level of purity. The characterization of electrocarboxylated compounds was done with spectroscopic techniques like IR, NMR (1H & 13C), mass and elemental analysis.
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- D.T. Yang, M. Zhu, Z.J. Schiffer, K. Williams, X. Song, X. Liu and K.Manthiram, ACS Catal., 9, 4699 (2019); https://doi.org/10.1021/acscatal.9b00818
- S.R. Waldvogel, S. Lips, M. Selt, B. Riehl and C.J. Kampf, Chem. Rev., 118, 6706 (2018); https://doi.org/10.1021/acs.chemrev.8b00233
- G. Yuan, L. Li, H. Jiang, C. Qi and F. Xie, Chin. J. Chem., 28, 1983 (2010); https://doi.org/10.1002/cjoc.201090331
- T. Fujihara, K. Nogi, T. Xu, J. Terao and Y. Tsuji, J. Am. Chem. Soc., 134, 9106 (2012); https://doi.org/10.1021/ja303514b
- P.P. Luo, Y.T. Zhang, B.L. Chen, S.X. Yu, H.W. Zhou, K.G. Qu, Y.X. Kong, X.Q. Huang, X.X. Zhang and J.X. Lu, catalysts, 7, 274 (2017); https://doi.org/10.3390/catal7090274
- O. Scialdone, A. Galia, C. Belfiore, G. Filardo and G. Silvestri, Ind. Eng. Chem. Res., 43, 5006 (2004); https://doi.org/10.1021/ie034275+
- A.K. Shil, S. Kumar, C.B. Reddy, S. Dadhwal, V. Thakur and P. Das, Org. Lett., 17, 5352 (2015); https://doi.org/10.1021/acs.orglett.5b02701
- S.L. Khaja, R.R. Ramesh, S.M. Krishna and J.S. Reddy, Synth. Commun., 36, 31 (2006); https://doi.org/10.1080/00397910500328811
- A.K. Datta, P.A. Marron, C.J.H. King and J.H. Wagenknecht, J. Appl. Electrochem., 28, 569 (1998); https://doi.org/10.1023/A:1003289800341
- O. Sock, M. Troupel and J. Perichon, Tetrahedron Lett., 26, 1509 (1985); https://doi.org/10.1016/S0040-4039(00)98538-1
- I. Reche, S. Mena, I. Gallardo and G. Guirado, Electrochim. Acta, 320, 134576 (2019); https://doi.org/10.1016/j.electacta.2019.134576
- Y. Hiejima, M. Hayashi, A. Uda, S. Oya, H. Kondo, H. Senboku and K. Takahashi, Phys. Chem. Chem. Phys., 12, 1953 (2010); https://doi.org/10.1039/b920413j
- G. Yuan, Z. Li and H. Jiang, Chin. J. Chem., 27, 1464 (2009); https://doi.org/10.1002/cjoc.200990246
- E. Duñach and J. Périchon, J. Organomet. Chem., 352, 239 (1988); https://doi.org/10.1016/0022-328X(88)83038-9
- G.Q. Yuan, H.F. Jiang and C. Lin, Tetrahedron, 64, 5866 (2008); https://doi.org/10.1016/j.tet.2008.04.053
- Z.Z. Yang, Y.N. Zhao, L.N. He, J. Gao and Z.S. Yin, Green Chem., 14, 519 (2012); https://doi.org/10.1039/c2gc16039k
- A. Ion, C.V. Doorslaer, V. Parvulescu, P. Jacobs and D.D. Vos, Green Chem., 10, 111 (2008); https://doi.org/10.1039/B711197E
- S. Mena, J. Sanchez and G. Guirado, RSC Advances, 9, 15115 (2019); https://doi.org/10.1039/C9RA01781J
- F.S. Mjalli, J. Naser, B. Jibril, V. Alizadeh and Z. Gano, J. Chem. Eng. Data, 59, 2242 (2014); https://doi.org/10.1021/je5002126
- E. Bjerglund, M. Kongsfelt, K. Shimizu, B.B.E. Jensen, L. Koefoed, M. Ceccato, T. Skrydstrup, S.U. Pedersen and K. Daasbjerg, Langmuir, 30, 6622 (2014); https://doi.org/10.1021/la501297j
- A.R. Fakhari, D. Nematollahi, M. Shamsipur, S. Makarem, S.S. Hosseini Davarani, A. Alizadeh and H.R. Khavasi, Tetrahedron, 63, 3894 (2007); https://doi.org/10.1016/j.tet.2007.02.023
- O. Scialdone, C. Amatore, A. Galia and G. Filardo, J. Electroanal. Chem., 592, 163 (2006); https://doi.org/10.1016/j.jelechem.2006.04.009
- S.F. Zhao, M.X. Zhu, K. Zhang, H. Wang and J.X. Lu, Tetrahedron Lett., 52, 2702 (2011); https://doi.org/10.1016/j.tetlet.2011.03.076
- A. Tortajada, F. JuliáHernández, M. Börjesson, T. Moragas and R. Martin, Angew. Chem. Int. Ed., 57, 15948 (2018); https://doi.org/10.1002/anie.201803186
- K. Sekine and T. Yamada, Chem. Soc. Rev., 45, 4524 (2016); https://doi.org/10.1039/C5CS00895F
- C.M. Williams, J.B. Johnson and T. Rovis, J. Am. Chem. Soc., 130, 14936 (2008); https://doi.org/10.1021/ja8062925
- D. Pletcher and L. Slevin, J. Chem. Soc., Perkin Trans. 2, 217 (1996); https://doi.org/10.1039/P29960000217
- C. Amatore, A. Jutand, F. Khalil and M.F. Nielsen, J. Am. Chem. Soc., 114, 7076 (1992); https://doi.org/10.1021/ja00044a018
References
D.T. Yang, M. Zhu, Z.J. Schiffer, K. Williams, X. Song, X. Liu and K.Manthiram, ACS Catal., 9, 4699 (2019); https://doi.org/10.1021/acscatal.9b00818
S.R. Waldvogel, S. Lips, M. Selt, B. Riehl and C.J. Kampf, Chem. Rev., 118, 6706 (2018); https://doi.org/10.1021/acs.chemrev.8b00233
G. Yuan, L. Li, H. Jiang, C. Qi and F. Xie, Chin. J. Chem., 28, 1983 (2010); https://doi.org/10.1002/cjoc.201090331
T. Fujihara, K. Nogi, T. Xu, J. Terao and Y. Tsuji, J. Am. Chem. Soc., 134, 9106 (2012); https://doi.org/10.1021/ja303514b
P.P. Luo, Y.T. Zhang, B.L. Chen, S.X. Yu, H.W. Zhou, K.G. Qu, Y.X. Kong, X.Q. Huang, X.X. Zhang and J.X. Lu, catalysts, 7, 274 (2017); https://doi.org/10.3390/catal7090274
O. Scialdone, A. Galia, C. Belfiore, G. Filardo and G. Silvestri, Ind. Eng. Chem. Res., 43, 5006 (2004); https://doi.org/10.1021/ie034275+
A.K. Shil, S. Kumar, C.B. Reddy, S. Dadhwal, V. Thakur and P. Das, Org. Lett., 17, 5352 (2015); https://doi.org/10.1021/acs.orglett.5b02701
S.L. Khaja, R.R. Ramesh, S.M. Krishna and J.S. Reddy, Synth. Commun., 36, 31 (2006); https://doi.org/10.1080/00397910500328811
A.K. Datta, P.A. Marron, C.J.H. King and J.H. Wagenknecht, J. Appl. Electrochem., 28, 569 (1998); https://doi.org/10.1023/A:1003289800341
O. Sock, M. Troupel and J. Perichon, Tetrahedron Lett., 26, 1509 (1985); https://doi.org/10.1016/S0040-4039(00)98538-1
I. Reche, S. Mena, I. Gallardo and G. Guirado, Electrochim. Acta, 320, 134576 (2019); https://doi.org/10.1016/j.electacta.2019.134576
Y. Hiejima, M. Hayashi, A. Uda, S. Oya, H. Kondo, H. Senboku and K. Takahashi, Phys. Chem. Chem. Phys., 12, 1953 (2010); https://doi.org/10.1039/b920413j
G. Yuan, Z. Li and H. Jiang, Chin. J. Chem., 27, 1464 (2009); https://doi.org/10.1002/cjoc.200990246
E. Duñach and J. Périchon, J. Organomet. Chem., 352, 239 (1988); https://doi.org/10.1016/0022-328X(88)83038-9
G.Q. Yuan, H.F. Jiang and C. Lin, Tetrahedron, 64, 5866 (2008); https://doi.org/10.1016/j.tet.2008.04.053
Z.Z. Yang, Y.N. Zhao, L.N. He, J. Gao and Z.S. Yin, Green Chem., 14, 519 (2012); https://doi.org/10.1039/c2gc16039k
A. Ion, C.V. Doorslaer, V. Parvulescu, P. Jacobs and D.D. Vos, Green Chem., 10, 111 (2008); https://doi.org/10.1039/B711197E
S. Mena, J. Sanchez and G. Guirado, RSC Advances, 9, 15115 (2019); https://doi.org/10.1039/C9RA01781J
F.S. Mjalli, J. Naser, B. Jibril, V. Alizadeh and Z. Gano, J. Chem. Eng. Data, 59, 2242 (2014); https://doi.org/10.1021/je5002126
E. Bjerglund, M. Kongsfelt, K. Shimizu, B.B.E. Jensen, L. Koefoed, M. Ceccato, T. Skrydstrup, S.U. Pedersen and K. Daasbjerg, Langmuir, 30, 6622 (2014); https://doi.org/10.1021/la501297j
A.R. Fakhari, D. Nematollahi, M. Shamsipur, S. Makarem, S.S. Hosseini Davarani, A. Alizadeh and H.R. Khavasi, Tetrahedron, 63, 3894 (2007); https://doi.org/10.1016/j.tet.2007.02.023
O. Scialdone, C. Amatore, A. Galia and G. Filardo, J. Electroanal. Chem., 592, 163 (2006); https://doi.org/10.1016/j.jelechem.2006.04.009
S.F. Zhao, M.X. Zhu, K. Zhang, H. Wang and J.X. Lu, Tetrahedron Lett., 52, 2702 (2011); https://doi.org/10.1016/j.tetlet.2011.03.076
A. Tortajada, F. JuliáHernández, M. Börjesson, T. Moragas and R. Martin, Angew. Chem. Int. Ed., 57, 15948 (2018); https://doi.org/10.1002/anie.201803186
K. Sekine and T. Yamada, Chem. Soc. Rev., 45, 4524 (2016); https://doi.org/10.1039/C5CS00895F
C.M. Williams, J.B. Johnson and T. Rovis, J. Am. Chem. Soc., 130, 14936 (2008); https://doi.org/10.1021/ja8062925
D. Pletcher and L. Slevin, J. Chem. Soc., Perkin Trans. 2, 217 (1996); https://doi.org/10.1039/P29960000217
C. Amatore, A. Jutand, F. Khalil and M.F. Nielsen, J. Am. Chem. Soc., 114, 7076 (1992); https://doi.org/10.1021/ja00044a018