Blue LED Mediated C-H and N-H Insertion of Indoles into Aryldiazoesters and Iodonium Ylides

被引：0
|
作者：
Gremaud, Ludovic [1 ]
Sen, Subhabrata [2 ]
机构：
[1] Univ Appl Sci Western Switzerland, Fac Engn & Architecture, Dept Chem, Perolles 80, CH-1700 Fribourg, Switzerland
[2] Shiv Nadar Univ, Sch Nat Sci, Dept Chem, Greater Noida 201314, Uttar Pradesh, India
来源：
CHIMIA | 2022年 / 76卷 / 05期
关键词：
Blue LED; C-H insertion; N-H insertion; Aryldiazoesters; Iodonium ylides; ANTICANCER; INHIBITORS; ANALOGS;
D O I：
10.2533/chimia.2022.483
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein we have discussed projects related to blue LED mediated C-H and N-H insertion reaction in indoles and related heterocycles with aryl diazoesters and iodonium ylides as sources of carbenes. Blue LED effectively facilitates these conversions and was optimized from the option of numerous other LED lights. No metal catalysts were required. The reactions provide formation of differently alkylated indoles, pyrroles and furans. Control experiments and DFT calculation were used to understand the mechanism of reactions. As an application compounds bearing azepino[4, 5-b]indole and spiropiperidino indole building blocks were synthesized from the alkylated products.
引用
收藏
页码：483 / 492
页数：10
相关论文
共 50 条
  • [41] Ruthenium-Catalyzed Vinylene Carbonate Annulation by C-H/N-H Functionalizations: Step-Economical Access to Indoles
    Yu, Yao
    Wang, Yang
    Li, Bo
    Tan, Yuqiang
    Zhao, Huan
    Li, Zheyu
    Zhang, Chunran
    Ma, Wenbo
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (04) : 838 - 844
  • [42] Catalytic additions of O-H, N-H and C-H bonds to alkenes
    Hartwig, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [43] CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C-H and N-H bonds of Arylamides
    Kalsi, Deepti
    Barsu, Nagaraju
    Sundararaju, Basker
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (10) : 2360 - 2364
  • [44] Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of N-methoxybenzamides with a Rh(iii)-catalyst
    Mayakrishnan, Sivakalai
    Tamizmani, Masilamani
    Maheswari, Naryanan Uma
    CHEMICAL COMMUNICATIONS, 2020, 56 (98) : 15462 - 15465
  • [45] Self-assembly of methacrylamides assisted by an interplay of N-H•••O, C-H•••O, C-H•••π and π-π interactions
    Venkataramanan, B
    Saifudin, MA
    J, VJ
    Suresh, V
    CRYSTENGCOMM, 2004, 6 : 284 - 289
  • [46] Rapid and accurate evaluation of the binding energies and the individual N-H···O=C, N-H···N, C-H···O=C, and C-H···N interaction energies for hydrogen-bonded peptide-base complexes
    CuiYing Huang
    Yang Li
    ChangSheng Wang
    Science China Chemistry, 2013, 56 : 238 - 248
  • [47] Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles
    Sabat, Nazarii
    Zhou, Weiping
    Gandon, Vincent
    Guinchard, Xavier
    Vincent, Guillaume
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (30)
  • [48] Rapid and accurate evaluation of the binding energies and the individual N-H•••O=C, N-H•••N, C-H•••O=C, and C-H•••N interaction energies for hydrogen-bonded peptide-base complexes
    Huang CuiYing
    Li Yang
    Wang ChangSheng
    SCIENCE CHINA-CHEMISTRY, 2013, 56 (02) : 238 - 248
  • [49] N-H VIS C-H ACTIVATION - A MAJOR LIGAND SIZE EFFECT
    SCHULZ, M
    MILSTEIN, D
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) : 318 - 319
  • [50] Direct Amination of Azoles via Catalytic C-H, N-H Coupling
    Monguchi, Daiki
    Fujiwara, Taiki
    Furukawa, Hirotoshi
    Mori, Atsunori
    ORGANIC LETTERS, 2009, 11 (07) : 1607 - 1610
12345