C-H bond chlorination and bromination using water soluble nickel(<sc>ii</sc>) guanidine complexes

被引:0
|
作者
Khatri, Jaipriya [1 ]
Mari, Vasanthapandiyan [1 ]
Sarkar, Aniruddha [2 ]
Karmodak, Naiwrit [1 ]
Dhar, Basab Bijayi [1 ]
机构
[1] Shiv Nadar Inst Eminence, Sch Nat Sci, Dept Chem, Dadri 201314, UP, India
[2] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, India
关键词
HALOGENATION;
D O I
10.1039/d4dt02783c
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Water-soluble nickel(ii)-guanidine-based complexes successfully catalyzed the C-H chlorination of a series of hydrocarbons in the presence of NaOCl and acetic acid in water-chloroform (7 : 3, biphasic condition) at room temperature. Majorly chlorinated products (TON similar to 680 for cyclohexane) were obtained. Furthermore, C-H bond bromination of cyclohexane, n-hexane, and toluene was also carried out using in situ generation of NaOBr. These putative formations of Ni(iii) species were characterized by electron paramagnetic resonance (EPR) spectroscopy, and the plausible mechanism for chlorination was confirmed by DFT calculations.
引用
收藏
页数:9
相关论文
共 50 条
  • [1] C-H bond chlorination using nickel(ii) complexes of tetradentate amido-quinoline ligands
    Adhikari, Sanjay
    Sarkar, Aniruddha
    Dhar, Basab Bijayi
    CHEMICAL COMMUNICATIONS, 2022, 58 (25) : 4075 - 4078
  • [2] Enantioselective C-H bond functionalization under Co(<sc>iii</sc>)-catalysis
    Garai, Bholanath
    Das, Abir
    Kumar, Doppalapudi Vineet
    Sundararaju, Basker
    CHEMICAL COMMUNICATIONS, 2024, 60 (25) : 3354 - 3369
  • [3] A mesoionic carbene stabilized nickel(<sc>ii</sc>) hydroxide complex: a facile precursor for C-H activation chemistry
    Pavun, Anna
    Niess, Raffael
    Scheibel, Lucas A.
    Seidl, Michael
    Hohloch, Stephan
    DALTON TRANSACTIONS, 2024, 53 (06) : 2749 - 2761
  • [4] A rhodium(<sc>ii</sc>)/rhodium(<sc>iii</sc>) redox couple for C-H bond amination with alkylazides: a rhodium(<sc>iii</sc>)-nitrenoid intermediate with a tetradentate [14]-macrocyclic ligand
    Sugimoto, Hideki
    Sakaida, Megumu
    Shiota, Yoshihito
    Miyanishi, Mayuko
    Morimoto, Yuma
    Yoshizawa, Kazunari
    Itoh, Shinobu
    DALTON TRANSACTIONS, 2024, 53 (04) : 1607 - 1615
  • [5] Rh(<sc>iii</sc>)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation
    Dash, Om Prakash
    Garg, Divya
    Volla, Chandra M. R.
    CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10576 - 10579
  • [6] Water-soluble luminescent platinum(<sc>ii</sc>) complexes for guanine quadruplex binding
    Kroos, Simon
    Hebenbrock, Marian
    Hepp, Alexander
    Layh, Marcus
    Lueke, Joschua
    Tonkul, Ali R.
    Strassert, Cristian A.
    Mueller, Jens
    DALTON TRANSACTIONS, 2025, 54 (13) : 5367 - 5390
  • [7] Fe(<sc>iii</sc>)-catalyzed p-selective C-H bond chalcogenation of phenols
    Paul, Biprajit
    Ghosh, Sayak
    Das, Surajit
    Chatterjee, Indranil
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (40) : 8133 - 8137
  • [8] Nickel complexes for catalytic C-H bond functionalization
    Johnson, S. A.
    DALTON TRANSACTIONS, 2015, 44 (24) : 10905 - 10913
  • [9] DFT study on Rh(<sc>ii</sc>)/guanidine-catalyzed asymmetric N-H bond insertion of benzophenone imines
    Xu, Jiaying
    Wei, Qi
    Hu, Changwei
    Su, Zhishan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (12) : 2896 - 2903
  • [10] Pd(<sc>ii</sc>)-catalyzed enantioselective C-H olefination and photoregulation of sterically hindered diarylethenes
    Zhang, Guanlun
    Wu, Xu
    Mao, Shiyu
    Li, Mengqi
    Hu, Honglong
    Shi, Bing-Feng
    Zhu, Wei-Hong
    CHEMICAL SCIENCE, 2024, 15 (47) : 20013 - 20021