Citation: Xu Dingjian, Meng Lichen, Xu Hang, Yao Xiaoquan. Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1205-1212. doi: 10.6023/cjoc201701051 shu

Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes

Xu Dingjian ^a ,
Meng Lichen ^a ,
Xu Hang ^a ,
Yao Xiaoquan ^a,*,,

a.
Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016

Corresponding author: Yao Xiaoquan, yaoxq@nuaa.edu.cn
Received Date: 27 January 2017
Revised Date: 21 March 2017

Fund Project: by the National Natural Science Foundation of China 21172107by the National Natural Science Foundation of China 21472092

Figures(1)

A copper iodide catalyzed reaction of aldehydes and t-butyl hydroperoxide (TBHP) was developed for the synthesis of peresters in the presence of bipyridine ligand under mild and neat conditions. The addition of bipyridine ligand increased the catalytic activities of copper catalyst significantly and triggered the reaction. The reaction showed good tolerance to various substrates, and good to excellent yields were obtained. Furthermore, a one-pot synthesis of allylic esters was also achieved by the addition of cyclohexene to the reaction mixture under neat condition at relative lower temperature.
- copper catalyzed,
- N-donor ligand,
- C-H activation,
- perester,
- allylic ester,
- one-pot synthesis,
- neat
1. [1]
2. [2]
  Some recent examples: (a) Sarkar, S.; Laha, R. M.; Mitra, R. N.; Maiti D. K. ACS Omega 2016, 1, 981. (b) Tang, S.; Zeng, L.; Liu, Y.; Lei, A. Angew. Chem., Int. Ed. 2015, 54, 15850. (c) Zhou, B.; Du, J.; Yang, Y.; Li, Y. Org. Lett. 2013, 15, 2934. (d) Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 332.
3. [3]
  Some examples: (a) Mo, J.; Wang, L.; Cui, X. Org. Lett. 2015, 17, 4960. (b) Spantulescu, M. D.; Boudreau, M. A.; Vederas, J. C. Org. Lett. 2009, 11, 645. (c) Yamago, S. J. Polym. Sci: Polym. Chem. Ed. 2006, 44, 1. (d) Wang, L.; Liu, X.; Li, Y. Langmuir 1998, 14, 6879. (e) Sosnovsky, G.; Zaret, E. H.; Konieczny, M. J. Org. Chem. 1972, 37, 2267 and the references therein.
4. [4]
  Lu, M. Y.; Bao, R.; Liu, W.; Li, Y. J. Org. Chem. 1995, 60, 5341. doi: 10.1021/jo00121a068
5. [5]
  Bolje, A.; Hohloch, S.; Urankar, D.; Pevec, A.; Gazvoda, M.; Sarkar, B.; Košmrlj, J. Organometallics 2014, 10, 2588.
6. [6]
  Zhang, H.; Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L. RSC Adv. 2016, 6, 8465. doi: 10.1039/C5RA27500H
7. [7]
  Wei, W.; Zhang, C.; Xu Y.; Wan, X. Chem. Commun. 2011, 47, 10827. doi: 10.1039/c1cc14602e
8. [8]
  (a) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819. For recent reviews see: (b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845. (c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
9. [9]
  A recent review: Krylov, I. B.; Vil', V. A.; Terent'ev, A. O. Beilstein J. Org. Chem. 2015, 11, 92.
10. [10]
  Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384. doi: 10.1021/ol3013606
11. [11]
  Zhou, J.; Jin, C.; Li, X.; Su, W. RSC Adv. 2015, 5, 7232. doi: 10.1039/C4RA14586K
12. [12]
  Tran, B. L.; Driess, M.; Hartwig J. F. J. Am. Chem. Soc. 2014, 136, 17292. doi: 10.1021/ja510093x
13. [13]
  Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2014, 16, 2530. doi: 10.1021/ol5009119
14. [14]
  Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086. doi: 10.1021/ol5011906
15. [15]
  García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-Dorado, F. J.; Ortega, M. J.; Massanet, G. M.; Guerra, F. M. Org. Lett., 2014, 16, 1598. doi: 10.1021/ol500198c
16. [16]
  Koschker, P.; Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011, 28, 20746.
17. [17]
  Thiery, E.; Aouf, C.; Belloy, J.; Harakat, D.; Bras, J. L.; Muzart, J. J. Org. Chem. 2010, 75, 1771. doi: 10.1021/jo902587u
18. [18]
  Recent reviews, see: Chem. Rev. 2008, 109(8), all of the articles therein; also see: Suzuki, M. Acc. Chem. Res. 2007, 40, 609.
19. [19]
  We also reported a series of reactions about the ligand effects on copper, silver and gold catalysts: (a) Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395. (b) Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953. (c) Yu, M.; Wang, Y.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2009, 50, 6791. (d) Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett 2011, 2363. (e) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Adv. Synth. Catal. 2012, 354, 71. (f) Wang, Y.; Wu, C.; Nie, S.; Xu, D.; Yao, X. Tetrahedron Lett. 2015, 56, 6827.
1. [1]
  Hui Zhang , Zijian Zhao , Yajing Wang , Kai Ni , Yanfei Wang , Liang Zhu , Jianyun Liu , Xiaoyu Zhao . Structurally engineered solvent-free LiFePO₄ electrodes via hot-pressing with efficient ion transport pathways for lithium extraction from brine. Acta Physico-Chimica Sinica, 2026, 42(2): 100130-0. doi: 10.1016/j.actphy.2025.100130
2. [2]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
3. [3]
  Wan JIANG , Shiman ZHAO , Wenting ZHANG , Duihai TANG . Mo₂N nanoparticles encapsulated with N-doped carbon materials: Synthesis by solvent-free method and hydrogen evolution electrocatalytic performance. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 906-916. doi: 10.11862/CJIC.20250348
4. [4]
  Mengyang LI , Zhonghao NIU , Hao XU , Jingli XIE . One-pot synthesis of 4H-pyran derivatives catalyzed by viologen-modified metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1513-1522. doi: 10.11862/CJIC.20250205
5. [5]
  Xinxin Dai , Di Lan , Xingliang Chen , Xingwei Wang , Guangbin Ji . One pot green synthesis and electromagnetic wave absorption performance of manganese dioxide@nitrogen-doped carbon@NiFe₂O₄ hybrids. Acta Physico-Chimica Sinica, 2026, 42(8): 100302-0. doi: 10.1016/j.actphy.2026.100302
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
8. [8]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
9. [9]
  Yuge Fan , Xianliang Fu , Li Zhu , Man Xu . Small changes, big differences: modified KSCN molten salt method for one-pot synthesis of Cd vacancy-enriched MoS₂/CdS and the enhanced photocatalytic H₂ evolution performance. Acta Physico-Chimica Sinica, 2026, 42(10): 100221-0. doi: 10.1016/j.actphy.2025.100221
10. [10]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
11. [11]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
12. [12]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
13. [13]
  Weimei Zeng , Youai Qiu . Electrochemical C-H carboxylation of benzylamines. Chinese Chemical Letters, 2026, 37(1): 111679-. doi: 10.1016/j.cclet.2025.111679
14. [14]
  Hailang JIA , Yujie LU , Pengcheng JI . Preparation and properties of nitrogen and phosphorus co-doped graphene carbon aerogel supported ruthenium electrocatalyst for hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2327-2336. doi: 10.11862/CJIC.20250021
15. [15]
  Yuan Xue , Yanjun Zhang , Jun Du , Zushun Xu , Guangfu Liao , Qing Li . Introducing dual-functional site on carbon nitride: steering carrier migration and O₂ activation for boosted H₂O₂ photosynthesis. Acta Physico-Chimica Sinica, 2026, 42(9): 100311-0. doi: 10.1016/j.actphy.2026.100311
16. [16]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
17. [17]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
18. [18]
  Haofan Niu , Yuhan Wu , Xinran Li , Longmei Li , Dong Wang , Yongce Zhang , Fengyu Liu , Wei Bai . 自驱动固体酸催化乙酸苄酯的合成. University Chemistry, 2026, 41(1): 1-8. doi: 10.12461/PKU.DXHX202505049
19. [19]
  Pengfei WANG , Qiuyan WU . Nano-sized 1D copper coordination polymer: Room-temperature solid-state synthesis and efficient adsorption performance toward Congo red dye. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2099-2108. doi: 10.11862/CJIC.20260150
20. [20]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(2363)
HTML views(292)

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