Citation: Fan Yuxin, Yao Yaoyao, Chen Rui, Zhao Ping, Tang Lei, Wang Cong, Wang Ying. K₂CO₃-Promoted C-S bonds Construction via Direct Coupling of Benzofuran Units with Thiols at 3-Position[J]. Chemistry, ;2018, 81(7): 610-615, 609. shu

K₂CO₃-Promoted C-S bonds Construction via Direct Coupling of Benzofuran Units with Thiols at 3-Position

Fan Yuxin ¹ ,
Yao Yaoyao ¹ ,
Chen Rui ¹ ,
Zhao Ping ¹ ,
Tang Lei ^1,2 ,
Wang Cong ^1,, ,
Wang Ying ^1,2,,

1.
School of Pharmacy, Guizhou Medical University, Guiyang 550004
2.
Guizhou Provincial Engineering Technology Research Center for Chemical Drug R & D, Guizhou Medical University, Guiyang 550004

Corresponding author: Wang Cong, 619624244@qq.com Wang Ying, 280622267@qq.com
Received Date: 6 February 2018
Accepted Date: 7 May 2018

Figures(3)

Based on the previous work, this paper further investigated the reaction of 2-position branched benzofuran units with thiol to form C-S bond at the 3-position. The study found that K₂CO₃ can efficiently promoted the reaction with benzofuran units to produce 3-arylthiobenzofuran derivatives which the functional groups at the 2-position are aliphatic ketones with different chain lengths. All the products were characterized by NMR and HRMS. The reaction has the advantages of mild reaction conditions, wide range of substrate application, simple operation, high yield, environmental friendliness and so on. It can provide a potential synthetic pathway for the synthesis of natural products containing aromatic sulfur-substituted groups and complex drug molecules.
- K₂CO₃-promoted,
- Benzofuran,
- C-S bonds
1. [1]
2. [2]
3. [3]
4. [4]
  K L Dunbar, D H Scharf, A Litomska et al. Chem. Rev., 2017, 117(8): 5521-5577.
5. [5]
6. [6]
  D Coskun, M Erkisa, E Ulukaya et al. Eur. J. Med. Chem., 2017, 136: 212-222.
7. [7]
  W J Wang, L Wang, Z Liu et al. Phytochemistry, 2016, 122: 238-245.
8. [8]
  T Singh Chundawat, N Sharma, S Bhagat. Med. Chem., 2014, 10(4): 409-417.
9. [9]
  C Aswathanarayanappa, E Bheemappa, Y D Bodke et al. Med. Chem. Res., 2013, 22(1): 78-87.
10. [10]
  J Zhao, H Fang, C Xie et al. J. Org. Chem., 2013, 2(12): 1044-1047.
11. [11]
  Y D Bodke, S Shankerrao, R Kenchappa et al. Russ. J. Gen. Chem., 2017, 87(8): 1843-1849.
12. [12]
  H A Du, X G Zhang, R Y Tang et al. J. Org. Chem., 2009, 74(20): 7844-7848.
13. [13]
  S Vásquez-Céspedes, A Ferry, L Candish et al. Angew. Chem. Int. Ed., 2015, 54(19): 5772-5776.
14. [14]
  C Wang, Y Fan, Y Yao et al. Chemistry Select, 2018, 3(1): 29-33.
15. [15]
  J P Bachelet, R Royer, P Gayral. Eur. J. Med. Chem. 1985, 20(5): 425-427.
1. [1]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
2. [2]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
3. [3]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
4. [4]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-. doi: 10.1016/j.actphy.2025.100052
5. [5]
  Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti₃C₂ electrode material used for H₂S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
6. [6]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
7. [7]
  Maomao Liu , Guizeng Liang , Ningce Zhang , Tao Li , Lipeng Diao , Ping Lu , Xiaoliang Zhao , Daohao Li , Dongjiang Yang . Electron-rich Ni2+ in Ni3S2 boosting electrocatalytic CO2 reduction to formate and syngas. Chinese Journal of Structural Chemistry, 2024, 43(8): 100359-100359. doi: 10.1016/j.cjsc.2024.100359
8. [8]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
9. [9]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
10. [10]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
11. [11]
  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
12. [12]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . ZnCoP/CdLa₂S₄肖特基异质结的构建促进光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-. doi: 10.3866/PKU.WHXB202404030
13. [13]
  Hao GUO , Tong WEI , Qingqing SHEN , Anqi HONG , Zeting DENG , Zheng FANG , Jichao SHI , Renhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co₉S₈/Ni₃S₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085
14. [14]
  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
15. [15]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-. doi: 10.1016/j.actphy.2025.100054
16. [16]
  Tieping CAO , Yuejun LI , Dawei SUN . Surface plasmon resonance effect enhanced photocatalytic CO₂ reduction performance of S-scheme Bi₂S₃/TiO₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 903-912. doi: 10.11862/CJIC.20240366
17. [17]
  Peng Li , Yuanying Cui , Zhongliao Wang , Graham Dawson , Chunfeng Shao , Kai Dai . Efficient interfacial charge transfer of CeO₂/Bi₁₉Br₃S₂₇ S-scheme heterojunction for boosted photocatalytic CO₂ reduction. Acta Physico-Chimica Sinica, 2025, 41(6): 100065-. doi: 10.1016/j.actphy.2025.100065
18. [18]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
19. [19]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016
20. [20]
  Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C₃N₄/O-doped-C₃N₅ for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1085)
HTML views(75)

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

K2CO3-Promoted C-S bonds Construction via Direct Coupling of Benzofuran Units with Thiols at 3-Position

Metrics

通讯作者: 陈斌, bchen63@163.com

K₂CO₃-Promoted C-S bonds Construction via Direct Coupling of Benzofuran Units with Thiols at 3-Position