Sulfated polyborate catalyzed rapid and efficient electrophilic thiocyanation of activated arenes

被引：6
|
作者：
Patil, Nilesh B. [1 ,2 ]
Chaturbhuj, Ganesh U. [1 ]
机构：
[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, India
[2] UPL Ltd, R&D Ctr, Wagle Ind Estate, Thana 400604, Maharashtra, India
来源：
TETRAHEDRON LETTERS | 2022年 / 96卷
关键词：
Electrophilic thiocyanation; Sulfated polyborate; Activated arenes; beta-ketoesters; SOLVENT-FREE SYNTHESIS; HETEROAROMATIC-COMPOUNDS; REGIOSELECTIVE THIOCYANATION; ENVIRONMENTALLY BENIGN; AROMATIC-COMPOUNDS; HIGHLY EFFICIENT; PROTOCOL; GREEN; BIOSYNTHESIS; DERIVATIVES;
D O I：
10.1016/j.tetlet.2022.153763
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This report describes a rapid, efficient, and environment-friendly methodology for electrophilic thiocyanation of activated arenes using sulfated polyborate as a Bronsted acid catalyst and H2O2 as a green oxidizer at 30 ?. The methodology was applied for activated arenes, including indoles and beta-ketoesters, along with recyclability of aqueous quench was demonstrated for four cycles with no loss of catalytic activity. The key benefits of the method are a shorter reaction time, higher yields, and easy work-up under mild reaction condition. (C) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Synthesis of arenes and heteroarenes by hydroarylation reactions catalyzed by electrophilic metal complexes
    de Mendoza, Paula
    Echavarren, Antonio M.
    PURE AND APPLIED CHEMISTRY, 2010, 82 (04) : 801 - 820
  • [32] Rapid, efficient and eco-friendly procedure for the synthesis of quinoxalines under solvent-free conditions using sulfated polyborate as a recyclable catalyst
    Indalkar, Krishna S.
    Khatri, Chetan K.
    Chaturbhuj, Ganesh U.
    JOURNAL OF CHEMICAL SCIENCES, 2017, 129 (02) : 141 - 148
  • [33] Rapid, efficient and eco-friendly procedure for the synthesis of quinoxalines under solvent-free conditions using sulfated polyborate as a recyclable catalyst
    KRISHNA S INDALKAR
    CHETAN K KHATRI
    GANESH U CHATURBHUJ
    Journal of Chemical Sciences, 2017, 129 : 141 - 148
  • [34] Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes
    Misal, Balu
    Palav, Amey
    Ganwir, Prerna
    Chaturbhuj, Ganesh
    TETRAHEDRON LETTERS, 2021, 74
  • [35] An efficient, environmentally benign, and solvent-free protocol for the synthesis of 4-substituted 1,5-benzodiazepines catalyzed by reusable sulfated polyborate
    Indalkar, Krishna S.
    Patil, Manisha S.
    Chaturbhuj, Ganesh U.
    TETRAHEDRON LETTERS, 2017, 58 (48) : 4496 - 4502
  • [36] Activated carbon-catalyzed hydrogenation of polycyclic arenes
    Sun, LB
    Zong, ZM
    Kou, JH
    Zhang, LF
    Ni, ZH
    Yu, GY
    Hong, C
    Wei, XY
    Lee, CW
    ENERGY & FUELS, 2004, 18 (05) : 1500 - 1504
  • [37] Me3SiCl-Catalyzed Electrophilic Thiocyanation/Cyclization of Alkynylbenzoates to Synthesize 4-Thiocyanatoisocourmarins
    Shao, Chukai
    He, Ying
    Yin, Hongquan
    Chen, Fu-Xue
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (05)
  • [38] Phosphoric Acid Catalyzed Electrophilic Thiocyanation of Indoles: Access to SCN-Containing Aryl-Indole Compounds
    Ye, Ai-Hui
    Li, Zi-Hao
    Ding, Tong-Mei
    Ke, Hua
    Chen, Zhi-Min
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (11)
  • [39] Sc(OTf)3 catalyzed electrophilic amination of arenes:: An expeditious synthesis of aryl hydrazides
    Yadav, JS
    Reddy, BVS
    Veerendhar, G
    Rao, RS
    Nagaiah, K
    CHEMISTRY LETTERS, 2002, (03) : 318 - 319
  • [40] Copper- Catalyzed Electrophilic Amination of Heteroarenes and Arenes by C-H Zincation**
    McDonald, Stacey L.
    Hendrick, Charles E.
    Wang, Qiu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (18) : 4667 - 4670
12345