Citation: Ali Reza Kiasat Roya Mirzajani, Haji Shalbaf, Tahereh Tabatabaei. Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst:An efficient and eco-friendly route to synthesis of b-hydroxy-thiocyanate[J]. Chinese Chemical Letters, ;2009, 20(9): 1026-1029. doi: 10.1016/j.cclet.2009.04.015 shu

Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst:An efficient and eco-friendly route to synthesis of b-hydroxy-thiocyanate

Chemistry Department, College of Science, Shahid Chamran University, Ahvaz 61357-4-3169, Iran

Received Date: 4 January 2009

A highly effective and mild protocol for ring opening of epoxides with NH ₄ SCN in the presence of catalytic amount of a multisite phase-transfer catalyst, α,α',α" -N-hexakis(triethylammoniummethylene chloride)-melamine, is developed. A variety of b-hydroxy thiocyanates as important intermediates in agricultural and pharmaceutical chemistry were obtained in high yields with excellent regioselectivity and in short reaction times.
- Multi-site phase-transfer catalyst,
- β-Hydroxythiocyanate,
- Thiocyanohydrin,
- Epoxide,
- Ring opening,
- Regioselectivity
1. [1]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
2. [2]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
3. [3]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
4. [4]
  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
5. [5]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
6. [6]
  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
7. [7]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
8. [8]
  Shuai Li , Liuting Zhang , Fuying Wu , Yiqun Jiang , Xuebin Yu . Efficient catalysis of FeNiCu-based multi-site alloys on magnesium-hydride for solid-state hydrogen storage. Chinese Chemical Letters, 2025, 36(1): 109566-. doi: 10.1016/j.cclet.2024.109566
9. [9]
  Zhenzhen Zhao , Meichen Jiao , Jiejie Ling , Han Jiang , Yan Gao , Hao Xu , Hai-Qing Li , Jingang Jiang , Peng Wu , Le Xu . Toward the microporous zeolite family with tunable large-medium cage and pore opening. Chinese Journal of Structural Chemistry, 2024, 43(9): 100336-100336. doi: 10.1016/j.cjsc.2024.100336
10. [10]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
11. [11]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
12. [12]
  Rui Liu , Yue Yu , Lu Deng , Maoxia Xu , Haorong Ren , Wenjie Luo , Xudong Cai , Zhenyu Li , Jingyu Chen , Hua Yu . The synergistic effect of A-site cation engineering and phase regulation enables efficient and stable Ruddlesden-Popper perovskite solar cells. Chinese Chemical Letters, 2024, 35(12): 109545-. doi: 10.1016/j.cclet.2024.109545
13. [13]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
14. [14]
  Xiuzheng Deng , Yi Ke , Jiawen Ding , Yingtang Zhou , Hui Huang , Qian Liang , Zhenhui Kang . Construction of ZnO@CDs@Co₃O₄ sandwich heterostructure with multi-interfacial electron-transfer toward enhanced photocatalytic CO₂ reduction. Chinese Chemical Letters, 2024, 35(4): 109064-. doi: 10.1016/j.cclet.2023.109064
15. [15]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
16. [16]
  Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
17. [17]
  Pengcheng Su , Shizheng Chen , Zhihong Yang , Ningning Zhong , Chenzi Jiang , Wanbin Li . Vapor-phase postsynthetic amination of hypercrosslinked polymers for efficient iodine capture. Chinese Chemical Letters, 2024, 35(9): 109357-. doi: 10.1016/j.cclet.2023.109357
18. [18]
  Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
19. [19]
  Mengjia Luo , Yi Qiu , Zhengyang Zhou . Exploring temperature-driven phase dynamics of phosphate: The periodic to incommensurately modulated long-range ordered phase transition in CsCdPO4. Chinese Journal of Structural Chemistry, 2025, 44(1): 100446-100446. doi: 10.1016/j.cjsc.2024.100446
20. [20]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(673)
HTML views(35)

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