Exploiting Transient Radical Cations as Bronsted Acids for Allylic C-H Heteroarylation of Enol Silyl Ethers

被引:15
|
作者
Nakashima, Tsubasa [1 ,2 ]
Fujimori, Haruka [1 ,2 ]
Ohmatsu, Kohsuke [1 ,2 ]
Ooi, Takashi [1 ,2 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648601, Japan
[2] Nagoya Univ, Grad Sch Engn, Dept Mol & Macromol Chem, Nagoya, Aichi 4648601, Japan
关键词
C-H functionalization; enol silyl ethers; heteroarylation; photoredox catalysis; radical cations; SUBSTITUTION-REACTION; ELECTRON-TRANSFER; ARYLATION; CYCLOADDITIONS; REACTIVITY;
D O I
10.1002/chem.202101352
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intermediary radical cations, generated through single-electron oxidation of enol silyl ethers by excited Ir-based photocatalysts, can be exploited as Bronsted acids for the activation of heteroarylcyanides. This strategy enables the direct allylic C-H heteroarylation of enol silyl ethers under visible-light irradiation.
引用
收藏
页码:9253 / 9256
页数:4
相关论文
共 50 条
  • [31] A simple method for quantitative estimation of C-H bond lengths in hydrocarbon radical cations
    Shchapin, IY
    Chuvylkin, ND
    RUSSIAN CHEMICAL BULLETIN, 1996, 45 (02) : 306 - 311
  • [32] Manganese-catalyzed enantioselective oxidation of C-H bonds of alkanes and silyl ethers to optically active ketones
    Murahashi, S
    Noji, S
    Hirabayashi, T
    Komiya, N
    TETRAHEDRON-ASYMMETRY, 2005, 16 (21) : 3527 - 3535
  • [33] Bronsted Acid Cocatalysts in Photocatalytic Radical Addition of α-Amino C-H Bonds across Michael Acceptors
    Espelt, Laura Ruiz
    Wiensch, Eric M.
    Yoon, Tehshik P.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 4107 - 4114
  • [34] Enantioselective Cyclization of 4-Alkenoic Acids via an Oxidative Allylic C-H Esterification
    Takenaka, Kazuhiro
    Akita, Mitsutoshi
    Tanigaki, Yugo
    Takizawa, Shinobu
    Sasai, Hiroaki
    ORGANIC LETTERS, 2011, 13 (13) : 3506 - 3509
  • [35] Enantioselective cyclization of 4-alkenoic acids via an oxidative allylic C-H esterification
    Akita, Mitsutoshi
    Tanigaki, Yugo
    Takenaka, Kazuhiro
    Takizawa, Shinobu
    Sasai, Hiroaki
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [36] Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C-H Functionalization
    Mai, Duy N.
    Baxter, Ryan D.
    ORGANIC LETTERS, 2016, 18 (15) : 3738 - 3741
  • [37] Radical Transformation of Aliphatic C-H Bonds to Oxime Ethers via Hydrogen Atom Transfer
    Wang, Xinmou
    Yu, Mo
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    ORGANIC LETTERS, 2021, 23 (21) : 8353 - 8358
  • [38] Free radical acylation approaches of C-H bonds with 2-chloroethylsulfonyl oxime ethers
    Kim, S
    Kim, N
    Chung, WJ
    Cho, CH
    SYNLETT, 2001, : 937 - 940
  • [39] 1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C-H Acid for Bronsted and Lewis Acid Catalysis
    Hoefler, Denis
    van Gemmeren, Manuel
    Wedemann, Petra
    Kaupmees, Karl
    Leito, Ivo
    Leutzsch, Markus
    Lingnau, Julia B.
    List, Benjamin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (05) : 1411 - 1415
  • [40] α-Silyl effects on the acidities of carbon acids and the homolytic bond dissociation enthalpies of their acidic C-H bonds
    Zhang, S.
    Zhang, X.-M.
    Bordwell, F.G.
    Journal of the American Chemical Society, 1995, 117 (02):