Citation: Yi Bo Huang, Wen Bin Yi, Chun Cai. An efficient, recoverable fluorous organocatalyst for accelerating the DABCO-promoted Morita-Baylis-Hillman reaction[J]. Chinese Chemical Letters, ;2011, 22(9): 1055-1058. doi: 10.1016/j.cclet.2011.03.010 shu

An efficient, recoverable fluorous organocatalyst for accelerating the DABCO-promoted Morita-Baylis-Hillman reaction

Yi Bo Huang ^a,b, ,
Wen Bin Yi ^a ,
Chun Cai ^a

a School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094, China;
b Department of Pharmacy, Changzhou Institute of Engineering Technology, Changzhou 213164, China

Received Date: 7 December 2010

Fund Project: We thank the project of "Excellence Initiative" and "Zijin Star" in NJUST, "Doctoral Fund of Ministry of Education of China" (No.200802881024), and "National Natural Science Foundation of China" (No.20902047) for financial support.

A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst l-[4- (perfluorooctyl)phenyll-3-phenylthiourea and DABCO at room temperature. The fluorous organocatalyst could be recovered from the reaction mixture by fluorous solid-phase extraction (F-SPE) with excellent purity for direct reuse.
- Organocatalyst,
- Morita-Baylis-Hillman reaction,
- Fluorous solid phase extraction (F-SPE)
1. [1]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
2. [2]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
3. [3]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
4. [4]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
5. [5]
  Dong-Sheng Deng , Su-Qin Tang , Yong-Tu Yuan , Ding-Xiong Xie , Zhi-Yuan Zhu , Yue-Mei Huang , Yun-Lin Liu . C-F insertion reaction sheds new light on the construction of fluorinated compounds. Chinese Chemical Letters, 2024, 35(8): 109417-. doi: 10.1016/j.cclet.2023.109417
6. [6]
  Hao Sun , Xiaoxue Li , Baoyu Wu , Kai Zhu , Yinyi Gao , Tianzeng Bao , Hongbin Wu , Dianxue Cao . Direct regeneration of spent LiFePO₄ cathode material via a simple solid-phase method. Chinese Chemical Letters, 2025, 36(6): 110041-. doi: 10.1016/j.cclet.2024.110041
7. [7]
  Quanyou Guo , Yue Yang , Tingting Hu , Hongqi Chu , Lijun Liao , Xuepeng Wang , Zhenzi Li , Liping Guo , Wei Zhou . Regulating local electron transfer environment of covalent triazine frameworks through F, N co-modification towards optimized oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(1): 110235-. doi: 10.1016/j.cclet.2024.110235
8. [8]
  Zhenguo Zhang , Lanyang Li , Xinlong Zong , Yongheng Lv , Shuanglei Liu , Liang Ji , Xuefei Zhao , Zhenhua Jia , Teck-Peng Loh . "Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model. Chinese Chemical Letters, 2025, 36(7): 110504-. doi: 10.1016/j.cclet.2024.110504
9. [9]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108
10. [10]
  Han Yan , Jingming Yao , Zhangran Ye , Qiaoquan Lin , Ziqi Zhang , Shulin Li , Dawei Song , Zhenyu Wang , Chuang Yu , Long Zhang . Al-F co-doping towards enhanced electrolyte-electrodes interface properties for halide and sulfide solid electrolytes. Chinese Chemical Letters, 2025, 36(1): 109568-. doi: 10.1016/j.cclet.2024.109568
11. [11]
  Jiawen Zhu , Yingge Hao , Zhen Song , Huina Zhou , Youmei Wang , Ling Yan , Minghua Lu . Synthesis of mesopore-rich hollow carbon nanospheres as headspace solid-phase microextraction coating to extract PAHs from water and honey. Chinese Chemical Letters, 2025, 36(12): 111290-. doi: 10.1016/j.cclet.2025.111290
12. [12]
  Zhuangzhuang Zhang , Yaru Qiao , Jun Zhao , Dai-Huo Liu , Mengmin Jia , Hongwei Tang , Liang Wang , Dongmei Dai , Bao Li . Fluorine-doped K_0.39Mn_0.77Ni_0.23O_1.9F_0.1 microspheres with highly reversible oxygen redox reaction for potassium-ion battery cathode. Chinese Chemical Letters, 2025, 36(3): 109907-. doi: 10.1016/j.cclet.2024.109907
13. [13]
  Ziling Jiang , Chen Liu , Jie Yang , Xia Li , Chaochao Wei , Qiyue Luo , Zhongkai Wu , Lin Li , Liping Li , Shijie Cheng , Chuang Yu . Designing F-doped Li₃InCl₆ electrolyte with enhanced stability for all-solid-state lithium batteries in a wide voltage window. Chinese Chemical Letters, 2025, 36(6): 109741-. doi: 10.1016/j.cclet.2024.109741
14. [14]
  Mengxiang Zhu , Tao Ding , Yunzhang Li , Yuanjie Peng , Ruiping Liu , Quan Zou , Leilei Yang , Shenglei Sun , Pin Zhou , Guosheng Shi , Dongting Yue . Graphene controlled solid-state growth of oxygen vacancies riched V₂O₅ catalyst to highly activate Fenton-like reaction. Chinese Chemical Letters, 2024, 35(12): 109833-. doi: 10.1016/j.cclet.2024.109833
15. [15]
  Yuan Yan , Lingqi Shen , Yu Wang , Bincheng Gong , Zuguang Li , Hongdeng Qiu . Development of switchable deep eutectic solvents: Applications in extraction of natural products. Chinese Chemical Letters, 2025, 36(11): 110845-. doi: 10.1016/j.cclet.2025.110845
16. [16]
  Yan-Ran Weng , Wen-Fu Tian , Wen-Jing Ding , Bi-He Ren , De-Hou Liu , Jia-Ying Tang , Feng Zhou , Xiao-Gang Chen , Xian-Jiang Song , Hui-Peng Lv , Yong Ai . Homochiral organic ferroelastics with plastic phase transition. Chinese Chemical Letters, 2025, 36(7): 110188-. doi: 10.1016/j.cclet.2024.110188
17. [17]
  Yu-Chen Fang , Jia-He Chen , Mi-Zhuan Li , Hui-Min Li , Mei Bai , Yong-Zheng Chen , Zi-Wei Gao , Wen-Yong Han . Forging of silaoxycarbocyclics by interrupted Catellani reaction. Chinese Chemical Letters, 2025, 36(7): 110474-. doi: 10.1016/j.cclet.2024.110474
18. [18]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
19. [19]
  Tianxia Chen , Yunhui Chen , Weiwei Li , Peipei Cen , Yan Guo , Jin Zhang , Cunding Kong , Xiangyu Liu . Fabricating AuAg-nanoparticles/ZIF-8 composites for selective detection and efficient extraction of dinitroaniline pesticides. Chinese Chemical Letters, 2025, 36(8): 110214-. doi: 10.1016/j.cclet.2024.110214
20. [20]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1200)
HTML views(42)

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

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return