Synthesis of tris(indolyl)methanes by using dimethyl carbonate as a single carbon source via C-H functionalization approach

被引:2
|
作者
Nath, Priyanka [1 ]
Deb, Mohit L. [2 ,3 ]
Baruah, Pranjal K. [1 ]
机构
[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India
[2] Univ Sci & Technol Meghalaya, Adv Res Ctr, Baridua 793101, Meghalaya, India
[3] Univ Sci & Technol Meghalaya, Dept Chem, Baridua 793101, Meghalaya, India
关键词
Tris(indolyl)methanes; Indoles; Dimethyl carbonate; Copper catalyst; Carbon source; INDOLES; EFFICIENT; BONDS; BIS; ENAMINES; IODINE;
D O I
10.1007/s11696-023-03150-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here, we report a copper acetate/tert-butyl hydroperoxide-mediated reaction of N-substituted indoles with dimethyl carbonate under heating to give tris(indolyl)methanes via alpha-C-H functionalization of the methoxy group of dimethyl carbonate. The central methine carbon in the product comes from the dimethyl carbonate molecule, which is used as a substrate as well as a reaction medium. The reaction uses a cheap and environmentally benign copper metal catalyst which makes the process useful. This is the first report of tris(indolyl)methane synthesis using dimethyl carbonate as a single carbon source.
引用
收藏
页码:1117 / 1124
页数:8
相关论文
共 50 条
  • [31] Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
    Zhao, Dan
    Wang, Yue
    Zhu, Min-Xue
    Shen, Qi
    Zhang, Lei
    Du, Yun
    Li, Jian-Xin
    RSC ADVANCES, 2013, 3 (26): : 10272 - 10276
  • [32] Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C-H Functionalization
    Srinivas, Bokka
    Shakeena, Kotari
    Kota, Durgeswari Lakkavarapu
    Abhinav, Valeti
    Eswar, Pyla
    Sravani, Rongali Geetha
    Kumar, Anandam Sampath Pavan
    Indukuri, Kiran
    Dhanaraju, Kumpatla Ayyappa
    Kumar, Muthyala Murali Krishna
    Alla, Santhosh Kumar
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) : 4458 - 4471
  • [33] Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp3 C-H Functionalization
    Vadagaonkar, Kamlesh S.
    Kalmode, Hanuman P.
    Prakash, Sattey
    Chaskar, Atul C.
    SYNLETT, 2015, 26 (12) : 1677 - 1682
  • [34] Synthesis of Indolines via Pd(II)-Catalyzed Amination of C-H Bonds Using Phl(OAc)2 as the Bystanding Oxidant
    Mei, Tian-Sheng
    Leow, Dasheng
    Xiao, Han
    Laforteza, Brian N.
    Yu, Jin-Quan
    ORGANIC LETTERS, 2013, 15 (12) : 3058 - 3061
  • [35] Micellar catalysis enabled synthesis of indolylbenzothiazoles and their functionalization via Mn(II)-catalyzed C2-H amination using pyridones
    Kumar, Sanjeev
    Satpute, Dinesh Parshuram
    Vaidya, Gargi Nikhil
    Nagpure, Mithilesh
    Lokhande, Shyam Kumar
    Meena, Deepak
    Kumar, Dinesh
    TETRAHEDRON LETTERS, 2020, 61 (25)
  • [36] Ruthenium-catalysed one-pot regio- and diastereoselective synthesis of pyrrolo[1,2-a]indoles via cascade C-H functionalization/annulation
    Singh, Sukhdev
    Butani, Himanshu H.
    Vachhani, Dipak D.
    Shah, Anamik
    Van der Eycken, Erik V.
    CHEMICAL COMMUNICATIONS, 2017, 53 (78) : 10812 - 10815
  • [37] Post-functionalization of graphitic carbon nitrides by grafting organic molecules: toward C-H bond oxidation using atmospheric oxygen
    Zhang, Pengfei
    Li, Haoran
    Wang, Yong
    CHEMICAL COMMUNICATIONS, 2014, 50 (48) : 6312 - 6315
  • [38] Selective Synthesis of Pyrano[3,2-b]indoles or Cyclopenta[b]indoles Tethered with Medium-Sized Rings via Cascade C-C σ-Bond Cleavage and C-H Functionalization
    Wang, Mengdan
    Yang, Yajie
    Yin, Liqiang
    Feng, Ye
    Li, Yanzhong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 683 - 692
  • [39] Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant
    Ding, Shengtao
    Shi, Zhuangzhi
    Jiao, Ning
    ORGANIC LETTERS, 2010, 12 (07) : 1540 - 1543
  • [40] Cp*Co(III)-Catalyzed oxidative [5+2] annulation: regioselective synthesis of 2-aminobenzoxepines via C-H/O-H functionalization of 2-vinylphenols with ynamides
    Han, Xiang-Lei
    Liu, Xu-Ge
    Lin, E.
    Chen, Yunyun
    Chen, Zhuangzhong
    Wang, Honggen
    Li, Qingjiang
    CHEMICAL COMMUNICATIONS, 2018, 54 (82) : 11562 - 11565