Chinese Journal of Organic Chemistry >
Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation
Received date: 2021-10-14
Revised date: 2021-12-08
Online published: 2021-12-15
Supported by
Guangxi Natural Science Foundation(2021GXNSFBA196041); Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology(2020KF04); Opening Project of Hunan Engineering Laboratory for Analysis and Drugs Development of Ethnomedicine in Wuling Mountains(hgxy2101)
A series of ester compounds were synthesized by direct oxidative coupling of aldehydes with alcohols. The electrosynthesis reaction can be carried out at room temperature without inert gas protection, external oxidants, N-heterocyclic carbene (NHC) catalyst and alkali (such as DBU (1,5-dizzabicyclo[5.4.0]undecen-5-ene)), etc. The oxidative esterification reaction processes in a simple and easily available undivided electrochemical cell and constant current mode. This protocol features mild reaction conditions, broad substrate scope, cheap and easily available starting materials, and simple operation, providing a new strategy for the green synthesis of ester compounds.
Shiyan Cheng , Chuhong Ou , Hongmin Lin , Junsong Jia , Haitao Tang , Yingming Pan , Guobao Huang , Xiujin Meng . Electrochemically Mediated Esterification of Aromatic Aldehydes with Aliphatic Alcohols via Anodic Oxidation[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4718 -4724 . DOI: 10.6023/cjoc202110019
| [1] | Hettikankanamalage, A. A.; Lassfolk, R.; Ekholm, F. S.; Leino, R.; Crich, D. Chem. Rev. 2020, 120, 7104. |
| [2] | Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, John Wiley & Sons, Inc., New York, 1999. |
| [3] | Otera, J.; Nishikido, J. J. Am. Chem. Soc. 2010, 132, 9221. |
| [4] | Sable, V.; Shah, J.; Sharma, A.; Kapdi, A. R. Chem. Asian J. 2019, 14, 2639. |
| [5] | Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. |
| [6] | (a) Liu, C.; Tang, S.; Zheng, L.; Liu, D.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5662. |
| [6] | (b) Zhu, L.; Ren, X.; Yu, Y.; Ou, P.; Wang, Z.-X.; Huang, X. Org. Lett. 2020, 22, 2087. |
| [6] | (c) Li, X.; Goh, T. W.; Li, L.; Xiao, C.; Guo, Z.; Zeng, X. C.; Huang, W. ACS Catal. 2016, 6, 3461. |
| [6] | (d) Suzuki, K.; Yamaguchi, T.; Matsushita, K.; Iitsuka, C.; Miura, J.; Akaogi, T.; Ishida, H. ACS Catal. 2013, 3,1845. |
| [6] | (e) Paul, B.; Khatun, R.; Sharma, S. K.; Adak, S.; Singh, G.; Das, D.; Siddiqui, N.; Bhandari, S.; Joshi, V.; Sasaki, T.; Bal, R. ACS Sustainable Chem. Eng. 2019, 7, 3982. |
| [6] | (f) Cheng, J.; Zhu, M.; Wang, C.; Li, J.; Jiang, X.; Wei, Y.; Tang, W.; Xue, D.; Xiao, J. Chem. Sci. 2016, 7, 4428. |
| [7] | (a) Sarkar, S. D.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190. |
| [7] | (b) Liu, B.; Yan, J.; Huang, R.; Wang, W.; Jin, Z.; Zanoni, G.; Zheng, P.; Yang, S.; Chi, Y. R. Org. Lett. 2018, 20, 3447. |
| [7] | (c) Wu, Z.; Jiang, D.; Wang, J. Org. Chem. Front. 2019, 6, 688. |
| [7] | (d) Carmine, G. D.; Ragno, D.; Massi, A.; D'Agostino, C. Org. Lett. 2020, 22, 4927. |
| [8] | (a) Gaspa, S.; Porcheddu, A.; Luca, L. D. Org. Lett. 2015, 17, 3666. |
| [8] | (b) Chun, S.; Chung, Y. K. Org. Lett. 2017, 19: 3787. |
| [8] | (c) Mühldorf, B.; Wolf, R. ChemCatChem 2017, 9, 920. |
| [8] | (d) Kozlov, K. S.; Romashov, L. V.; Ananikov, V. P. Green Chem. 2019, 21, 3464. |
| [9] | (a) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. |
| [9] | (b) Moeller, K. D. Chem. Rev. 2018, 118, 4817. |
| [9] | (c) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 5594. |
| [9] | (d) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492. |
| [9] | (e) Yoshida, J.; Shimizu, A.; Hayashi, R. Chem. Rev. 2018, 118, 4702. |
| [9] | (f) Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27. |
| [9] | (g) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. |
| [9] | (h) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. |
| [9] | (i) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. |
| [9] | (j) Zhou, Y.-J.; Zhao, Z.-H.; Zeng, L.; Li, L.; He, Y.-H.; Gu, L.-J. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese) |
| [9] | ( 周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41, 1072.) |
| [9] | (k) Meng, Z.-Y.; Feng, C.-T.; Xu, K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese) |
| [9] | ( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.) |
| [9] | (l) Wu, M.; Yu, L.; Hou, H.-Q.; Chen, H.-Z.; Zhuang, Q.-L.; Zhou, S.-Y.; Lin, X.-Y. Chin. J. Org. Chem. 2021, 41, 2326. (in Chinese) |
| [9] | ( 吴媚, 于玲, 侯慧青, 陈厚铮, 庄庆龙, 周孙英, 林小燕, 有机化学, 2021, 41, 2326.) |
| [9] | (m) Liu, W.-Q.; Yang, X.-L.; Tong, Z.-H.; Wu, L.-Z. Acta Chim. Sinica 2019, 77, 861. (in Chinese) |
| [9] | ( 刘文强, 杨修龙, 佟振合, 吴骊珠, 化学学报, 2019, 77, 861.) |
| [9] | (n) Ma, Y.; Wu, S.; Jiang, S.; Xiao, F.; Deng, G.-J. Chin. J. Chem. 2021, 39, 3334. |
| [9] | (o) Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19. |
| [9] | (p) Chen, N.; Xu, H.-C. Green Synth. Catal. 2021, 2, 165. |
| [9] | (q) Wu, Y.; Chen, J.-Y.; Liao, H.-R.; Shu, X.-R.; Duan, L.-L.; Yang, X.-F.; He, W.-M. Green Synth. Catal. 2021, 2, 233. |
| [9] | (r) Chen, J.-Y.; Wu, H.-Y.; Gui, Q.-W.; Yan, S.-S.; Deng, J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. J. Catal. 2021, 42, 1445. |
| [10] | Finney, E. E.; Ogawa, K. A.; Boydston, A. J. J. Am. Chem. Soc. 2012, 134, 12374. |
| [11] | Green, R. A.; Pletcher, D.; Leach, S. G.; Brown, R. C. D. Org. Lett. 2015, 17, 3290. |
| [12] | (a) Zhong, P.-F.; Lin, H.-M.; Wang, L.-W.; Mo, Z.-Y.; Meng, X.-J.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2020, 22, 6334. |
| [12] | (b) He, M.-X.; Mo, Z.-Y.; Wang, Z.-Q.; Cheng, S.-Y.; Xie, R.-R.; Tang, H.-T.; Pan, Y.-M. Org. Lett. 2020, 22, 724. |
| [12] | (c) Li, Q.-Y.; Cheng, S.-Y.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2019, 21, 5517. |
| [12] | (d) Meng, X.-J.; Zhong, P.-F.; Wang, Y.-M.; Wang, H.-S.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2020, 362, 506. |
| [12] | (e) Zhang, Y.-Z.; Mo, Z.-Y.; Wang, H.-S.; Wen, X.-A.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2019, 21, 3807. |
| [12] | (f) Mo, Z.-Y.; Swaroop, T. R; Tong, W.; Zhang, Y.-Z.; Tang, H.-T.; Pan, Y.-M.; Sun, H.-B.; Chen, Z.-F. Green Chem. 2018, 20, 4428. |
| [13] | Sawamura, T.; Takahashi, K.; Inagi, S.; Fuchigami, T. Angew. Chem., Int. Ed. 2012, 51, 4413. |
| [14] | Xie, C.; Lin, L., Huang, L.; Wang, Z.; Jiang, Z.; Zhang, Z.; Han, B. Nat. Commun. 2021, 12, 4823. |
| [15] | Teng, B.; Shi, J.; Yao, C. Green Chem. 2018, 20, 2465. |
| [16] | Yu, D.; To, W.-P.; Tong, G. S. M.; Wu, L.-L.; Chan, K.-T.; Du, L.; Phillips, D. L.; Liu, Y.; Che, C.-M. Chem. Sci. 2020, 11, 6370. |
| [17] | Wang, L.; Neumann, H.; Spannenberg, A.; Beller, M. Chem. Commun. 2017, 53, 7469. |
| [18] | Yang, H. S.; Macha, L.; Ha, H.-J.; Yang, J. W. Org. Chem. Front. 2021, 8, 53. |
| [19] | Khosravi, K.; Khalaji, K.; Naserifar, S. J. Chin. Chem. Soc. 2017, 64, 303. |
| [20] | Yu, C.; Özkaya, B.; Patureau, F. W. Chem.-Eur. J. 2021, 27, 3682. |
| [21] | Lawson, J. R.; Wilkins, L. C.; Melen, R. L. Chem.-Eur. J. 2017, 23, 10997. |
| [22] | Veatch, A. M.; Alexanian, E. J. Chem. Sci. 2020, 11, 7210. |
| [23] | Bourne-Branchu, Y.; Gosmini, C.; Danoun, G. Chem.-Eur. J. 2017, 23, 10043. |
| [24] | Silva, A. T. M.; Pereira, V. V.; Takahashi, J. A.; Silva, R. R.; Duarte, L. P. Nat. Prod. Res. 2018, 32, 1714. |
| [25] | Hoque, M. E.; Hassan, M. M. M.; Chattopadhyay, B. J. Am. Chem. Soc. 2021, 143, 5022. |
| [26] | Rysak, V.; Dixit, R.; Trivelli, X.; Merle, N.; Agbossou-Niedercorn, F.; Kumar, V.; Michon, C. Cat. Sci. Technol. 2020, 10, 4586. |
| [27] | Rammurthy, B.; Peraka, S.; Vasu, A.; Sai, G. K.; Rohini, Y. D.; Narender, N. Asian J. Org. Chem. 2021, 10, 594. |
| [28] | Velasco, N.; Suárez, A.; Martínez-Lara, F.; Fernández-Rodríguez, M. Á.; Sanz, R.; Suárez-Pantiga, S. J. Org. Chem. 2021, 86, 7078. |
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