Electrochemical 1,2-hydrogen atom transfer functionalizations of N-(benzyloxy)phthalimides

被引:1
|
作者
Fu, Xin [1 ]
Ran, Tingting [1 ]
Liu, Jie [1 ,2 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China
[2] Hunan Univ, Greater Bay Area Inst Innovat, Guangzhou 511300, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 23期
基金
中国国家自然科学基金;
关键词
C-H FUNCTIONALIZATION; HYDROGEN-ATOM; ALKOXYL RADICALS; SELECTIVE FUNCTIONALIZATION; ORGANIC ELECTROSYNTHESIS; C(SP(3))-H BONDS; OXIDATION; HETEROARYLATION; REARRANGEMENT; REACTIVITY;
D O I
10.1039/d4qo01607f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a straightforward, catalyst-free method for the cathodic benzylic C-H hydroxyalkylation/arylation of N-(alkyloxy)phthalimides with ketones or cyanopyridines. The reaction is driven by an electrochemically induced 1,2-hydrogen atom transfer involving alkoxy radicals generated by O-N bond cleavage. This protocol provides an efficient approach for the synthesis of a wide range of valuable unsymmetrical 1,2-diols and diarylmethanols.
引用
收藏
页码:6760 / 6767
页数:8
相关论文
共 50 条
  • [21] 1,2-HYDROGEN SHIFT IN NEUTRON-IRRADIATED DICHLOROETHANES
    BEREI, K
    JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (05): : 717 - 718
  • [22] ANTIPSYCHOTIC PROPERTIES OF NEW N-(4-SUBSTITUTED-1-PIPERAZINYLETHYL)-PHTHALIMIDES AND N-(4-SUBSTITUTED-1-PIPERIDINYLETHYL)-PHTHALIMIDES
    ALRASHOOD, KA
    MUSTAFA, AA
    ALHAIDER, AA
    GINAWI, OT
    MADANI, AAE
    ELOBEID, HA
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1988, 77 (10) : 898 - 901
  • [23] HARDNESS PROFILES OF SOME 1,2-HYDROGEN SHIFT REACTIONS
    KAR, T
    SCHEINER, S
    JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (20): : 8121 - 8124
  • [24] REACTION-MECHANISM OF 1,2-HYDROGEN MIGRATION OF HYDROGEN-PEROXIDE
    BOSCH, E
    LLUCH, JM
    BERTRAN, J
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (05): : 666 - 673
  • [25] Visible-light-driven net-1,2-hydrogen atom transfer of amidyl radicals to access β-amido ketone derivatives
    Jiang, Yonggang
    Li, Hui
    Tang, Haoqin
    Zhang, Qingyue
    Yang, Haitao
    Pan, Yu
    Zou, Chenggang
    Zhang, Hongbin
    Walsh, Patrick J.
    Yang, Xiaodong
    CHEMICAL SCIENCE, 2025, 16 (02) : 962 - 969
  • [26] Facile rearrangement of metallacyclopentatrienes to butadienyl carbenes by a 1,2-hydrogen shift
    Becker, E
    Rüba, E
    Mereiter, K
    Schmid, R
    Kirchner, K
    ORGANOMETALLICS, 2001, 20 (18) : 3851 - 3853
  • [27] Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations
    Chang, Liang
    Wang, Shun
    An, Qing
    Liu, Linxuan
    Wang, Hexiang
    Li, Yubo
    Feng, Kaixuan
    Zuo, Zhiwei
    CHEMICAL SCIENCE, 2023, 14 (25) : 6841 - 6859
  • [28] Organic Photoredox-Catalyzed Site-Selective Alkylation of Glycine Derivatives and Peptides via Infrequent 1,2-Hydrogen Atom Transfer of Amidyl Radicals
    Hou, Jinyu
    Fan, Hongying
    Zhang, Xue
    Liu, Xingyu
    Chen, Jian
    Lv, Guanghui
    He, Shiyun
    Hai, Li
    Yang, Zhongzhen
    Wu, Yong
    ORGANIC LETTERS, 2024, 26 (36) : 7638 - 7643
  • [29] Photoinduced Single Electron Transfer Cyclization Reactions of N-(ω-Tributylstannylpolyethoxyether)phthalimides
    Jin Yingxue
    Yuan Wang
    Qu Fengyu
    Yoon, Ung Chan
    Wei Shunquan
    Yue Qunfeng
    Tan Guanghui
    ACTA CHIMICA SINICA, 2011, 69 (20) : 2407 - 2412
  • [30] ACTIVATION-ENERGY FOR A 1,2-HYDROGEN SHIFT IN (PHENOXYMETHYL)CHLOROCARBENE
    CHATEAUNEUF, JE
    LIU, MTH
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20): : 5942 - 5943