Mechanisms of Csp3-H functionalization of ethyl 2-(methyl(p-tolyl)amino)acetate: A theoretical investigation

被引：12
|
作者：
Zhou, Da-Gang [1 ]
Zhou, Pan-Pan [1 ]
Jing, Huan-Wang [1 ]
机构：
[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
来源：
COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2017年 / 1118卷
基金：
中国国家自然科学基金;
关键词：
Ethyl 2-(methyl(p-tolyl)amino)acetate; DFT; TRIARYLPHOSPHINE RADICAL CATIONS; FRONTIER-ELECTRON THEORY; GENERAL-METHOD; ISATINS; ACTIVATION; REACTIVITY; INDIRUBIN; OXIDATION; BONDS;
D O I：
10.1016/j.comptc.2017.09.003
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The mechanisms for the Csp(3)-H functionalization of ethyl 2-(methyl(p-tolyl)amino)acetate have been investigated using DFT method at the M06-2X/6-31+G(d, p) level, and the SMD model was applied to simulate the solvent effect. The computational results show that the Csp3-H functionalization has four possible paths to generate intermediate radical. Then addition reaction happens between the radical and O-2 molecule. Finally, the addition product can convert into 1,5-dimethylindoline-2,3-dione via two different paths. The results could provide valuable insights into these types of interactions and related ones. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码：144 / 152
页数：9
相关论文
共 50 条
  • [1] Mechanisms of Csp3-H functionalization of acetonitrile or acetone with coumarins: A DFT investigation
    Zhou, Da-Gang
    MOLECULAR CATALYSIS, 2020, 498
  • [2] Syntheses and crystal structures of 2-(p-tolyl)-1H-perimidine hemihydrate and 1-methyl-2-(p-tolyl)-1H-perimidine
    Kalle, Paulina
    Tatarin, Sergei, V
    Kiseleva, Marina A.
    Zakharov, Alexander Yu
    Smirnov, Daniil E.
    Bezzubov, Stanislav, I
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2022, 78 : 169 - +
  • [3] DFT investigation on the mechanisms of Csp3-H functionalization of glycine derivatives induced by radical cation salt
    Zhou, Da-Gang
    Wang, Peng
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (07) : 2833 - 2846
  • [4] Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(p-tolyl)methyl]amino}-3-phenylpropanoate
    Zhang, Xin
    Huang, Meng
    Du, Cong
    Han, Junjing
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O273 - U1634
  • [5] 2-(p-tolyl)-1,3,2-benzodioxaborole
    Bramham, G
    Batsanov, AS
    Marder, TB
    Norman, NC
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O972 - O973
  • [6] Dimethyl(2-{[2,3-di(p-tolyl)-5-methyl-1-indenylidene ](p-tolyl)methyl}-5-methoxy-phenylmethyl)amine
    Fernandez-G, J.M.
    Solorzano-Maldonado, K.
    Panneerselvam, K.
    Rodriguez-Romero, A.
    Soriano-Garcia, M.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1996, 52 (pt 2):
  • [7] Dimethyl(2-{[2,3-di(p-tolyl)-5-methyl-1-indenylidene] (p-tolyl)methyl}-5-methoxy-phenylmethyl)amine
    FernandezG, JM
    SolorzanoMaldonado, K
    Panneerselvam, K
    RodriguezRomero, A
    SorianoGarcia, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 460 - 462
  • [8] MOLECULAR-STRUCTURE OF 2-(P-TOLYL)AMINO-5,6-BENZO-2H-CHROMENE
    UTENYSHEV, AN
    CHUEV, II
    ALDOSHIN, SM
    KOZINA, OA
    RUSSIAN CHEMICAL BULLETIN, 1993, 42 (03) : 469 - 471
  • [9] Mechanisms of Csp3-H or Nsp2-H functionalization of 2,3-diaminoindoles with triplet O2: A density functional theory investigation
    Deng, Zhe-Peng
    Zhou, Da-Gang
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2021, 34 (02)
  • [10] Triflic acid-catalyzed Csp3-H functionalization of 2-methyl azaarenes with a α-trifluoromethyl imino ester
    Blocker, Mark
    Immaneni, Supriya
    Shaikh, Abid
    TETRAHEDRON LETTERS, 2014, 55 (40) : 5572 - 5575
12345