Lateral lithiation in deep eutectic solvents: regioselective functionalization of substituted toluene derivatives

被引:33
|
作者
Arnodo, Davide [1 ]
Ghinato, Simone [1 ]
Nejrotti, Stefano [1 ]
Blangetti, Marco [1 ]
Prandi, Cristina [1 ]
机构
[1] Univ Torino, Dipartimento Chim, Via P Giuria 7, I-10125 Turin, Italy
关键词
AROMATIC TERTIARY AMIDES; ATROPOSELECTIVITY; METALATION; REACTIVITY; BENZAMIDES; CHEMISTRY;
D O I
10.1039/d0cc00593b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The heteroatom-directed lateral lithiation of functionalized toluenes in a choline chloride-based eutectic mixture is reported. The metalations proceed within ultrafast reaction times, with a broad substrate and electrophile scope. The directing groups provide a rapid and high regioselective access to functionalized aromatic derivatives of remarkable synthetic value.
引用
收藏
页码:2391 / 2394
页数:4
相关论文
共 50 条
  • [21] Green electrosynthesis of bis(indolyl)methane derivatives in deep eutectic solvents
    Adly, Mina E.
    Mahmoud, Amr M.
    El-Nassan, Hala B.
    BMC CHEMISTRY, 2024, 18 (01)
  • [22] REGIOSELECTIVE FUNCTIONALIZATION OF N-PHTHALOYL-SUBSTITUTED AMINO-ACID AND PEPTIDE DERIVATIVES
    EASTON, CJ
    HUTTON, CA
    ROSITANO, G
    TAN, EW
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19): : 5614 - 5618
  • [24] Separation of toluene from a toluene/n-heptane mixture using ethylene glycol containing deep eutectic solvents
    YoonKook Park
    Korean Journal of Chemical Engineering, 2021, 38 : 604 - 609
  • [25] Functionalization of CNTs surface with phosphonuim based deep eutectic solvents for arsenic removal from water
    AlOmar, Mohamed Khalid
    Alsaadi, Mohammed Abdulhakim
    Hayyan, Maan
    Akib, Shatirah
    Hashim, Mohd Ali
    APPLIED SURFACE SCIENCE, 2016, 389 : 216 - 226
  • [26] Prototropic forms of hydroxy derivatives of naphthoic acid within deep eutectic solvents†
    Khokhar, Vaishali
    Pandey, Siddharth
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (15) : 9096 - 9108
  • [27] Experimental Investigation of Liquid-Liquid Extraction of Toluene plus Heptane or Toluene plus Hexane Using Deep Eutectic Solvents
    Hosseini, Amir
    Haghbakhsh, Reza
    Raeissi, Sona
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2019, 64 (09): : 3811 - 3820
  • [28] Pyridine Ionic Liquid-Based Deep Eutectic Solvents Selectively Separating Toluene from Alkanes
    Wu, Xiaojia
    Shi, JunJun
    Yu, Hui
    Li, Qunsheng
    Zhou, Zhiyong
    Ren, Zhongqi
    ENERGY & FUELS, 2023, 37 (06) : 4233 - 4243
  • [29] Absorption of Volatile Organic Compounds Toluene and Acetaldehyde in Choline Chloride-Based Deep Eutectic Solvents
    Indra, Sandipa
    Subramanian, Ranga
    Daschakraborty, Snehasis
    JOURNAL OF PHYSICAL CHEMISTRY B, 2022, 126 (20): : 3705 - 3716
  • [30] Deep Eutectic Solvents for the Separation of Toluene/1-Hexene via Liquid-Liquid Extraction
    Hadj-Kali, Mohamed K.
    El Blidi, Lahssen
    Mulyono, Sarwono
    Wazeer, Irfan
    Ali, Emad
    Rallapalli, Jagan
    SEPARATIONS, 2022, 9 (11)