Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

被引:6
|
作者
Das, Krishna Kanta [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati Cent Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
CROSS-COUPLING REACTIONS; C-H SILYLATION; SILICON CHEMISTRY; BOND; FUNCTIONALIZATION; HETEROARENES; DERIVATIVES; DESIGN; ACCESS;
D O I
10.1039/d3ob01925j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free, visible-light-mediated C-H silylation of 2H-indazoles with triphenylsilane has been developed employing 4CzIPN as a photocatalyst and triisopropylsilanethiol as a hydrogen atom transfer (HAT) reagent under aerobic reaction conditions. This method shows tolerance toward many functional groups and affords a variety of silylated indazoles at up to 89% yield. The experimental results suggest that the reaction progresses through a radical pathway.
引用
收藏
页码:1034 / 1037
页数:4
相关论文
共 50 条
  • [21] Recent synthetic approaches to 1H- and 2H-indazoles (microreview)
    Rai, Gaurav S.
    Maru, Jayesh J.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 973 - 975
  • [22] Direct observation of the photoinduced hydrogen atom transfer in 2'-hydroxychalcone
    Arai, T
    Norikane, Y
    CHEMISTRY LETTERS, 1997, (04) : 339 - 340
  • [23] Synthesis of 2H-Indazoles by the [3+2] Cycloaddition of Arynes and Sydnones
    Wu, Chunrui
    Fang, Yuesi
    Larock, Richard C.
    Shi, Feng
    ORGANIC LETTERS, 2010, 12 (10) : 2234 - 2237
  • [24] Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis
    Yu, Wan-Lei
    Luo, Yong-Chun
    Yan, Lei
    Liu, Dan
    Wang, Zhu-Yin
    Xu, Peng-Fei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) : 10941 - 10945
  • [25] Remote difunctionalization of 2H-indazoles using Koser's reagents
    Bhattacharjee, Suvam
    Laru, Sudip
    Hajra, Alakananda
    CHEMICAL COMMUNICATIONS, 2022, 58 (07) : 981 - 984
  • [26] Organophotoredox-Catalyzed Direct C-H Amination of 2H-Indazoles with Amines
    Neogi, Sukanya
    Ghosh, Asim Kumar
    Majhi, Koushik
    Samanta, Sadhanendu
    Kibriya, Golam
    Hajra, Alakananda
    ORGANIC LETTERS, 2020, 22 (14) : 5605 - 5609
  • [27] Benzylic C-H heteroarylation of 4-Methylphenols with 2H-Indazoles
    Yuan, Cheng
    Chen, Dongdong
    Pan, Changduo
    Yu, Jin-Tao
    TETRAHEDRON LETTERS, 2022, 105
  • [28] Controllable chemoselectivity in the reaction of 2H-indazoles with alcohols under visible-light irradiation: synthesis of C3-alkoxylated 2H-indazoles and ortho-alkoxycarbonylated azobenzenes
    Sun, Mingli
    Li, Laiqiang
    Wang, Lei
    Huo, Jie
    Sun, Manman
    Li, Pinhua
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (15): : 4230 - 4236
  • [29] Cobaloximes under H2: Kinetics of hydrogen atom transfer and catalysis of radical cycloisomerizations
    Li, Gang
    Han, Arthur
    Pulling, Mary E.
    Estes, Deven P.
    Norton, Jack R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [30] The nickel-catalyzed C3-acylation of 2H-indazoles with aldehydes
    Liu, Yan-Ling
    Pan, You-Lu
    Li, Gang-Jian
    Xu, Hai-Feng
    Chen, Jian-Zhong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (38) : 8749 - 8755