Desulfonylative Radical Truce-Smiles Rearrangement Utilizing the Benzimidazoline and Benzimidazolium Redox Couple

被引：0
|
作者：
Miyajima, Ryo [1 ]
Okamura, Manon [1 ]
Oomori, Kazuki [1 ]
Iwamoto, Hajime [1 ]
Wakamatsu, Kan [2 ]
Hasegawa, Eietsu [1 ]
机构：
[1] Niigata Univ, Fac Sci, Dept Chem, 8050 Ikarashi 2,Nishi Ku, Niigata 9502181, Japan
[2] Okayama Univ Sci, Fac Sci, Dept Chem, 1-1 Ridai Cho,Kita Ku, Okayama 7000005, Japan
来源：
SYNLETT | 2024年 / 35卷 / 03期
基金：
日本学术振兴会;
关键词：
benzimidazoline and benzimidazolium redox couple; single-electron transfer; photoreducing catalyst; radical Truce-Smiles rearrangement; desulfonylative aryl migration; PHOTOINDUCED ELECTRON-TRANSFER; TRANSFER PROBES; HYDROGEN-ATOM; LEAVING GROUP; ALPHA; REDUCTION; HYDRIDE; ELECTROCHEMISTRY; TRANSITION; CLEAVAGE;
D O I：
10.1055/a-2153-6594
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed protocols for promoting redox reactions utilizing the 2-substituted 1,3-dimethylbenzimidazoline (BIH-R) and benzimidazolium (BI*-R) couples which were applied to the desulfonylative radical Truce-Smiles rearrangement. Expected rearrangement products formed in modest to good yields in these processes, in which added or in situ generated BIH-R serve as electron-and hydrogen-atom-donating reagents or photocatalysts. DFT calculations were carried out to gain the information about the radical intermediates involved in the rearrangement reaction.
引用
收藏
页码：352 / 356
页数：5
相关论文
共 35 条
  • [1] A truce on the Smiles rearrangement: revisiting an old reaction-the Truce-Smiles rearrangement
    Snape, Timothy J.
    CHEMICAL SOCIETY REVIEWS, 2008, 37 (11) : 2452 - 2458
  • [2] A homologous enolate Truce-Smiles rearrangement
    Mitchell, LH
    Barvian, NC
    TETRAHEDRON LETTERS, 2004, 45 (29) : 5669 - 5671
  • [3] Truce-Smiles rearrangement of substituted phenyl ethers
    Kosowan, Joel R.
    W'Giorgis, Zemane
    Grewal, Ravneet
    Wood, Tabitha E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6754 - 6765
  • [4] The Truce-Smiles rearrangement and related reactions: a review
    Henderson, Anna R. P.
    Kosowan, Joel R.
    Wood, Tabitha E.
    CANADIAN JOURNAL OF CHEMISTRY, 2017, 95 (05) : 483 - 504
  • [5] Photoredox Radical Truce-Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides
    Tian, Lin
    Chen, Pu
    Ji, Xiaochen
    Deng, Guo-Jun
    Huang, Huawen
    ORGANIC LETTERS, 2024, 27 (01) : 455 - 461
  • [6] Truce-Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids
    Wang, Yu
    Pan, Wanying
    Zhang, Yuxuan
    Wang, Limin
    Han, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
  • [7] EXAMPLE OF ALKYL GROUP TRANSFER IN A TRUCE-SMILES REARRANGEMENT
    SNYDER, DM
    TRUCE, WE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) : 5432 - 5433
  • [8] Photocatalytic Difunctionalization of Vinyl Ureas by Radical Addition Polar Truce-Smiles Rearrangement Cascades
    Abrams, Roman
    Clayden, Jonathan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11600 - 11606
  • [9] Photocatalytic Asymmetric Acyl Radical Truce-Smiles Rearrangement for the Synthesis of Enantioenriched α-Aryl Amides
    Ma, Wei-Yang
    Leone, Matteo
    Derat, Etienne
    Retailleau, Pascal
    Reddy, Chada Raji
    Neuville, Luc
    Masson, Geraldine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (37)
  • [10] Effect of the tether length upon Truce-Smiles rearrangement reactions
    Fuss, David
    Wu, Yu Qi
    Grossi, Michael R.
    Hollett, Joshua W.
    Wood, Tabitha E.
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2018, 31 (01)
1234