Citation: Lü Wenwena, He Xinchuna, Shi Mina, Wang Feijun. Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 532-537. doi: 10.6023/cjoc201807024 shu

Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols

Lü Wenwena ^a ,
He Xinchuna ^a ,
Shi Mina ^a,b ,
Wang Feijun ^a,,

a.
School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Wang Feijun, feijunwang@ecust.edu.cn
Received Date: 16 July 2018
Revised Date: 4 September 2018
Available Online: 26 February 2018
Fund Project: the Shanghai Pujiang Program 16PJD017the National Natural Science Foundation of China 21372075Project supported by the National Natural Science Foundation of China (No. 21372075) and the Shanghai Pujiang Program (No. 16PJD017)

Figures(4)

Reaction of 2-(1-hydroxy-1-arylalkyl)phenols with anhydride and NEt₃ was reported, providing a practical way to the synthesis of ortho-acyloxy diarylalkenes, which is an important motif in many bioactive compounds and starting materials in many organic synthesis. This reaction can be achieved in one pot reaction under mild conditions in good yields.
- 2-(1-hydroxy-1-arylalkyl)phenols,
- ortho-acyloxy diarylalkenes,
- mild conditions,
- anhydride promoted reaction
1. [1]
  Jain, N. K.; Krishnamurty, H. G. Indian J. Chem., Sect. B 2000, 39, 817.
2. [2]
  Arnone, A.; Modugno, V. D.; Nasini, G.; Pava, O. V. Gazz. Chim. Ital. 1990, 120, 397.
3. [3]
  Shaiq, A. M.; Shaukat, M.; Shaista, P.; Uddin, A. U.; Hafeez, G. Phytochemistry 1999, 50, 1385. doi: 10.1016/S0031-9422(98)00480-4
4. [4]
  (a) Zheng, Y.-L.; Liu, Y.-Y.; Wu, Y.-M.; Wang, Y.-X. Lin, Y.-T.; Ye, M.-C. Angew. Chem., Int. Ed. 2016, 55, 6315.
  (b) Botteghi, C.; Corrias, T.; Marchetti, M.; Paganelli, S.; Piccolo, O. Org. Process Res. dev. 2002, 6, 379.
5. [5]
  (a) Zhang, Z.; Ju, T.; Miao, M.; Han, J.-L.; Zhang, Y.-H.; Zhu, X.-Y.; Ye, J.-H.; Yu, D.-J.; Zhi, Y.-G. Org. Lett. 2017, 19, 396.
  (b) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
  (c) Li, J.-F.; Chang, W.-J.; Ren, W.-L.; Liu, W.; Wang, H.-N.; Shi, Y. Org. Biomol. Chem. 2015, 13, 10341.
6. [6]
  (a) Ghorai, J.; Reddy, A. C. S.; Anbarasan, P. Chem.-Eur. J. 2016, 22, 16042.
  (b) Yang, D.-J.; Zhu, Y.-F.; Yang, N.; Jiang, Q.-Q.; Liu, R.-H. Adv. Synth. Catal. 2016, 358, 1731.
  (c) Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016, 72, 3022.
7. [7]
  (a) Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Li, X.-S.; Zhang, H.-R.; Zhu, X.-Y.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 3866.
  (b) Casanova, N.; Seoane, A.; MascareÇas, J. L.; Gulias, M. Angew. Chem., Int. Ed. 2015, 54, 2374.
8. [8]
  (a) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-G.; Lin, Z.-Y.; Sun, J.-W. J. Am. Chem. Soc. 2015, 137, 383.
  (b) Chen, J.-H.; Chen, C.-H.; Ji, C.-L.; Lu, Z. Org. Lett. 2016, 18, 1594.
9. [9]
  Nicolaou, K. C.; Snyder, S. A.; Huang, X.-H.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162. doi: 10.1021/ja040090y
10. [10]
  Kaswan, P.; Shelke, M. G.; Rao, K. V.; Kumar, A. Synlett 2016, 27, 2553. doi: 10.1055/s-0035-1560559
11. [11]
  Wang, Z.-N.; He, X.-X.; Zhang, R.; Zhang, G.; Xu, G. X.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2017, 19, 3067.
12. [12]
  Han, P.; Wang, R.-J.; Wang, D. Z. Tetrahedron 2011, 67, 8873. doi: 10.1016/j.tet.2011.09.073
13. [13]
  Zhang, Q.; Zheng, G.-F.; Zhang, Q; Li, Y. J. Org. Chem. 2017, 82, 8258. doi: 10.1021/acs.joc.7b01089
14. [14]
  Xie, J.; Li, J.; Weingand, V.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2016, 22, 12646. doi: 10.1002/chem.v22.36
15. [15]
  Moure, M. J.; Martin, R. S.; Dominguez, E. Angew. Chem., Int. Ed. 2012, 57, 3220.
16. [16]
  (a) Haldar, S.; Koner, S. Beilstein J. Org. Chem. 2013, 9, 49.
  (b) Tochigi, A.; Tsukamoto, K.; Suzuki, N.; Masuyama, Y. Eur. J. Org. Chem. 2016, 5678.
17. [17]
  Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016, 72, 3022. doi: 10.1016/j.tet.2016.04.018
18. [18]
  Zou, Y.-J.; Qin, L.-N.; Ren, X.-F.; Lu, Y.-P.; Li, Y.-X.; Zhou, J.-R. Chem. Eur. J. 2013, 19, 3504. doi: 10.1002/chem.201203646
19. [19]
  Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2003, 1091.
20. [20]
  Hamze, A.; Veau, D.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2009, 74, 1337. doi: 10.1021/jo802460z
21. [21]
  Roche, M.; Hamze, A.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2013, 78, 445. doi: 10.1021/jo3023268
22. [22]
  (a) Zhang, Y.; He, Y.; Li, L.-S.; Ji, M.-M.; Li, X.-Z.; Zhu, G.-G. J. Org. Chem. 2018, 83, 2898.
  (b) Hu, F.-D.; Xia, Y.; Ye, F.; Liu, Z.-X.; Ma, C.; Zhang, Y.; Wang, J.-B. Angew. Chem., Int. Ed. 2014, 53, 1364.
23. [23]
  Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954. doi: 10.1021/ja405503y
24. [24]
  (a) Brady, W. T.; Giang, Y. F. J. Org. Chem. 1985, 50, 5177.
  (b) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-Y.; Lin, Z.-Y.; Sun, Z.-W. J. Am. Chem. Soc. 2015, 137, 383.
  (c) Ogawa, N.; Yamaoka, Y.; Yamada, K.; Takasu, K. Org. Lett. 2017, 19, 3327.
25. [25]
  (a) Chiang, Y.; Jerry, K. A. Org. Biomol. Chem. 2004, 2, 1090.
  (b) Uchida, M.; Kuma, M.; Irie, M. Bull. Chem. Soc. Jpn. 1996, 69, 1023.
  (c) Guo, L.; Zhang, F.-Y.; Hu, W.-M.; Lia, L.; Jia, Y.-X. Chem. Commun. 2014, 50, 3299.
  (d) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
26. [26]
  Hull, F. J.; Balcells, D.; Sauer, L. O. E.; Raynaud, C.; Brudvig, W. G.; Crabtree, H. R.; Eisenstein, O. J. Am. Chem. Soc. 2010, 132, 7605. doi: 10.1021/ja908744w
27. [27]
  Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954. doi: 10.1021/ja405503y
1. [1]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
2. [2]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
3. [3]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
4. [4]
  Bowen Xu , Jiahao Chen , Lulu Cui , Xinyue Li , Yuan Xue , Sheng Han . Terpolymers of alkyl methacrylate-trans anethole-1,2,3,6-tetrahydrophthalic anhydride copolymers: A low dosage and high-efficiency cold flow improver for diesel fuel. Chinese Chemical Letters, 2025, 36(5): 110196-. doi: 10.1016/j.cclet.2024.110196
5. [5]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
6. [6]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
7. [7]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
8. [8]
  Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO₂ and NH₃. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
9. [9]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
10. [10]
  Ruonan Yang , Jiajia Li , Dongmei Zhang , Xiuqi Zhang , Xia Li , Han Yu , Zhanhu Guo , Chuanxin Hou , Gang Lian , Feng Dang . Grain-refining Co_0.85Se@CNT cathode catalyst with promoted Li₂O₂ growth kinetics for lithium-oxygen batteries. Chinese Chemical Letters, 2024, 35(12): 109595-. doi: 10.1016/j.cclet.2024.109595
11. [11]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
12. [12]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
13. [13]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
14. [14]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
15. [15]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
16. [16]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
17. [17]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
18. [18]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
19. [19]
  Qian Wang , Ting Gao , Xiwen Lu , Hangchao Wang , Minggui Xu , Longtao Ren , Zheng Chang , Wen Liu . Nanophase separated, grafted alternate copolymer styrene-maleic anhydride as an efficient room temperature solid state lithium ion conductor. Chinese Chemical Letters, 2024, 35(7): 108887-. doi: 10.1016/j.cclet.2023.108887
20. [20]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(604)
HTML views(47)

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