Citation: Menggen qiqige, Wu Yun, Bao Yongsheng. Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 902-911. doi: 10.6023/cjoc201710034 shu

Metal-Free Esterification of Aldehydes or Carboxylic Acids with Quaternary Ammonium Salts

College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot 010022

Corresponding author: Bao Yongsheng, sbbys197812@163.com
Received Date: 26 October 2017
Revised Date: 26 November 2017
Available Online: 5 April 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21462031) and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (No. NJYT-17-A22)the National Natural Science Foundation of China 21462031the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region NJYT-17-A22

Figures(3)

A metal-free esterification of various aldehydes or carboxylic acids with quaternary ammonium salts has been developed for selective synthesis of esters. A possible mechanism containing radical process that aldehyde converts to carboxylic acid and the generation of iodohydrocarbon via C-N bond cleavage of quaternary ammonium salt is proposed.
- quaternary ammonium salt,
- esterification,
- aldehyde
1. [1]
  (a) Cassar, L. ; Foa, M. ; Gardano, A. J. Organomet. Chem. 1976, 121, C55.
  (b) Bhardwaj, M. ; Sahi, S. ; Mahajan, H. ; Paul, S. ; Clark, J. H. J. Mol. Catal. A: Chem. 2015, 408, 48.
  (c) Zhang, J. T. ; Li, D. Y. ; Chen, H. ; Wang, B. J. ; Liu, Z. X. ; Zhang, Y. H. Adv. Synth. Catal. 2016, 358, 792.
2. [2]
  (a) Wang, X. ; Zhu, L. Z. ; Chen, S. H. ; Xu, X. H. ; Au, C. T. ; Qiu, R. Org. Lett. 2015, 17, 5228.
  (b) Lin, C. L. ; Li, D. ; Wang, Y. B. ; Yao, J. Z. ; Zhang, Y. H. Org. Lett. 2015, 17, 1328.
  (c) Fabrizi, G. ; Goggiamani, A. ; Sferrazza, A. ; Cacchi, S. Angew. Chem. , Int. Ed. 2010, 49, 4067.
  (d) Thirupathi, N. ; Puri, S. ; Reddy, T. J. ; Sridhar, B. ; Reddya, M. S. Adv. Synth. Catal. 2016, 358, 303.
  (e) Xu, P. ; Han, F. S. ; Wang, Y. H. Adv. Synth. Catal. 2015, 357, 3441.
  (f) Gadge, S. T. ; Khedkar, M. V. ; Lanke, S. R. ; Bhanage, B. M. Adv. Synth. Catal. 2012, 354, 2049.
3. [3]
  (a) Hirao, T. ; Yamada, N. ; Ohshiro, Y. ; Agawa, T. J. Organomet. Chem. 1982, 236, 409.
  (b) Hosomi, A. ; Hoashi, K. ; Kohra, S. ; Tominaga, Y. ; Otaka, K. ; Sakurai, H. J. Chem. Soc. , Chem. Commun. 1987, 570.
  (c) Bao, H. ; Qi, X. ; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206.
4. [4]
  (a) Wenkert, E. ; Han, A. -L. ; Jenny, C. -J. J. Chem. Soc. , Chem. Commun. 1988, 975.
  (b) Reeves, J. T. ; Fandrick, D. R. ; Tan, Z. ; Song, J. J. ; Lee, H. ; Yee, N. K. ; Senanayake, C. H. Org. Lett. 2010, 12, 4388.
  (c) Guo, W. -J. ; Wang, Z. -X. Tetrahedron 2013, 69, 9580.
5. [5]
  (a) Blakey, S. B. ; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
  (b) Maity, P. ; Shacklady-McAtee, D. M. ; Yap, G. P. A. ; Sirianni, E. R. ; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280.
6. [6]
  (a) Xie, L. -G. ; Wang, Z. -X. Angew. Chem. , Int. Ed. 2011, 50, 4901.
  (b) Zhang, X. -Q. ; Wang, Z. -X. J. Org. Chem. 2012, 77, 3658.
7. [7]
  Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448. doi: 10.1039/c3ob41989d
8. [8]
  (a) Uyanik, M. ; Ishihara, K. ChemCatChem 2012, 4, 177.
  (b) Xue, Q. C. ; Xie, J. ; Li, H. M. ; Cheng, Y. X. ; Zhu, C. J. Chem. Commun. 2013, 49, 3700.
  (c) Zhao, D. ; Wang, T. ; Shen, Q. ; Li, J. X. Chem. Commun. 2014, 50, 4302.
  (d) Wei, W. ; Zhang, C. ; Xu, Y. ; Wan, X. B. Chem. Commun. 2011, 47, 10827.
  (e) Liu, L. H. ; Yun, L. ; Wang, Z. K. ; Fu, X. F. ; Yan, C. H. Tetrahedron Lett. 2013, 54, 5383.
  (f) Li, D. J. ; Yang, T. H. ; Su, H. L. ; Yu, W. Adv. Synth. Catal. 2015, 357, 2529.
  (g) Hao, W. J. ; Du, Y. ; Wang, D. ; Jiang, B. ; Gao, Q. ; Tu, S. J. ; Li, G. G. Org. Lett. 2016, 18, 1884.
  (h) Zhang, H. ; Dong, D. Q. ; Hao, S. H. ; Wang, Z. L. RSC Adv. 2016, 6, 8465.
  (i) Sun, J. W. ; Wang, Y. ; Pan, Y. J. Org. Chem. 2015, 80, 8945.
  (j) Uyanik, M. ; Okamoto, H. ; Yasui, T. ; Ishihara, K. Science 2010, 328, 1376.
  (k) Kim, H. J. ; Kim, J. ; Cho, S. H. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382.
  (l) Rao, H. ; Ma, X. ; Liu, Q. ; Li, Z. ; Cao, S. ; Li, C. -J. Adv. Synth. Catal. 2013, 355, 2191.
9. [9]
  Wei, W.; Zhang, C.; Xu, Y.; Wan, X. Chem. Commun. 2011, 47, 10827. doi: 10.1039/c1cc14602e
10. [10]
  Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem., Int. Ed. 2012, 51, 3231. doi: 10.1002/anie.v51.13
11. [11]
  Zhao, J.; Li, P.; Xia, C.; Li, F. Chem. Commun. 2014, 50, 4751. doi: 10.1039/c4cc01587h
12. [12]
  Deshidi, R.; Rizvi, M. A.; Shah, B. A. RSC Adv. 2015, 5, 90521. doi: 10.1039/C5RA17425B
13. [13]
  Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538. doi: 10.1002/anie.201205921
14. [14]
  Huang, J.; Li, L.; Li, H.; Husan, E.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 10204. doi: 10.1039/c2cc35450k
15. [15]
  (a) Fox, S. C. ; Li, B. ; Xu, D. ; Edgar, K. J. Biomacromolecules 2011, 12, 1956.
  (b) Otera, J. ; Nishikido, J. Esterification, Methods, Reactions, and Applications, 2nd ed., Wiley-VCH, Weinheim, 2010.
  (c) Otera, J. Chem. Rev. 1993, 93, 1449.
  (d) Swamy, K. C. K. ; Kumar, N. N. B. ; Balaraman, E. ; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
16. [16]
  Kouichi, M.; Hayato, S.; Yu, M.; Kazuaki, S.; Fumi, H.; Yuki, Y.; Hirotsugu, M.; Keiji, N.; Shigenori, K. J. Oleo Sci. 2014, 63, 539. doi: 10.5650/jos.ess13199
17. [17]
  Kong, W.; Li, B.; Xu, X.; Song, Q. J. Org. Chem. 2016, 81, 8436. doi: 10.1021/acs.joc.6b01594
18. [18]
  Wang, Q.; Wang, Z.; Xu, Y.; Zhang, X.; Fan, X. Asian J. Org. Chem. 2016, 5, 1304. doi: 10.1002/ajoc.v5.11
19. [19]
  Nulty, J.; Nair, J. J.; Sliwinski, M.; Robertson, A. J. Tetrahedron Lett. 2009, 50, 2342. doi: 10.1016/j.tetlet.2009.02.200
20. [20]
  Blanc, P. Y.; Perret, A.; Teppa, F. Helv. Chim. Acta 1964, 47, 567. doi: 10.1002/hlca.19640470224
21. [21]
  Nishii, Y.; Akiyama, S.; Kita, Y.; Mashima, K. Synlett 2015, 26, 1831. doi: 10.1055/s-00000083
22. [22]
  Tahmasbi, B.; Ghorbani-Choghamarani, A. Catal. Lett. 2017, 147, 649. doi: 10.1007/s10562-016-1927-y
23. [23]
  Cho, C. S.; Kim, D. T.; Choi, H.; Kim, T.; Shim, S. C. Bull. Korean Chem. Soc. 2002, 23, 539. doi: 10.5012/bkcs.2002.23.4.539
24. [24]
  Lu, B.; Zhu, F.; Sun, H.; Shen, Q. Org. Lett. 2017, 19, 1132. doi: 10.1021/acs.orglett.7b00148
25. [25]
  Gaspa, S.; Porcheddu, A.; De Luca, L. Org. Lett. 2015, 17, 3666. doi: 10.1021/acs.orglett.5b01579
26. [26]
  Subrao, M.; Potukuchi, D. M.; Ramachandra, G.; Bhagavath, P.; Bhat, S. G.; Maddasani, S. Beilstein J. Org. Chem. 2015, 11, 233. doi: 10.3762/bjoc.11.26
27. [27]
  Liu, H.; Eisen, M. S. Organometallics 2017, 36, 1461. doi: 10.1021/acs.organomet.7b00101
28. [28]
  Beller, M.; Magerlein, W.; Indolese, A. F.; Fischer, C. Synthesis 2001, 1098.
29. [29]
  Zhu, Z.; Yuan, J.; Zhou, Y.; Qin, Y.; Xu, J.; Peng, Y. Eur. J. Org. Chem. 2014, 2014, 511.
30. [30]
  Bhandari, K. S.; Snieckus, V. Can. J. Chem. 1971, 49, 2354. doi: 10.1139/v71-380
1. [1]
  Mengfan Zhang , Lingyan Liu , Peng Wei , Wei Feng , Tao Yi . A proximity tagging strategy utilizing an activated aldehyde group as the active site. Chinese Chemical Letters, 2025, 36(4): 110127-. doi: 10.1016/j.cclet.2024.110127
2. [2]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
3. [3]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
4. [4]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
5. [5]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
6. [6]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
7. [7]
  Yuhao Zhou , Siyuan Wu , Xiaozhe Ren , Hongjin Li , Shu Li , Tianying Yan . Effects of salt fraction on the Na⁺ transport in salt-in-ionic liquid electrolytes. Chinese Chemical Letters, 2025, 36(6): 110048-. doi: 10.1016/j.cclet.2024.110048
8. [8]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
9. [9]
  Kailong Zhang , Chao Zhang , Luanhui Wu , Qidong Yang , Jiadong Zhang , Guang Hu , Liang Song , Gaoran Li , Wenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618
10. [10]
  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
11. [11]
  Ya-Ling Li , Jia-Wei Ke , Yue Liu , Dong-Mei Yao , Jing-Dong Zhang , You-Cai Xiao , Fen-Er Chen . Asymmetric conjugated addition of aryl Grignard reagents for the construction of chromanones bearing quaternary stereogenic centers in batch and flow. Chinese Chemical Letters, 2025, 36(6): 110377-. doi: 10.1016/j.cclet.2024.110377
12. [12]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
13. [13]
  Junhan Luo , Qi Qing , Liqin Huang , Zhe Wang , Shuang Liu , Jing Chen , Yuexiang Lu . Non-contact gaseous microplasma electrode as anode for electrodeposition of metal and metal alloy in molten salt. Chinese Chemical Letters, 2024, 35(4): 108483-. doi: 10.1016/j.cclet.2023.108483
14. [14]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
15. [15]
  Jiao Wang , Shuang-Yan Lang , Zhen-Zhen Shen , Gui-Xian Liu , Jian-Xin Tian , Yuan Li , Rui-Zhi Liu , Rui Wen . In situ imaging of the interfacial processes manipulated by salt concentration on zinc anodes in zinc metal batteries. Chinese Chemical Letters, 2025, 36(4): 109815-. doi: 10.1016/j.cclet.2024.109815
16. [16]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
17. [17]
  Ningning Gao , Yue Zhang , Zhenhao Yang , Lijing Xu , Kongyin Zhao , Qingping Xin , Junkui Gao , Junjun Shi , Jin Zhong , Huiguo Wang . Ba²⁺/Ca²⁺ co-crosslinked alginate hydrogel filtration membrane with high strength, high flux and stability for dye/salt separation. Chinese Chemical Letters, 2024, 35(5): 108820-. doi: 10.1016/j.cclet.2023.108820
18. [18]
  Hong Chen , Mao-Yin Ran , Long-Hua Li , Xin-Tao Wu , Hua Lin . [Cs14Cl][Tm71Se110]: An unusual salt-inclusion chalcogenide containing different valent Tm centers and ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100397-100397. doi: 10.1016/j.cjsc.2024.100397

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1435)
HTML views(148)

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