Metal-Free Transformation of Sulfonyl Oxime Ethers with Amines to Oxime Ethers

被引:6
|
作者
Zhang, Jia-Yuan [1 ]
Hu, Jinglin [1 ]
Li, Xiao-Xuan [1 ]
Tang, Wei-Ke [1 ]
Feng, Yi-Si [1 ,2 ]
机构
[1] Hefei Univ Technol, Sch Chem & Chem Engn, Anhui Prov Key Lab Adv Catalyt Mat & React Engn S, Hefei 230009, Peoples R China
[2] Anhui Prov Lab Heterocycl Chem, Maanshan 243110, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 18期
基金
中国国家自然科学基金;
关键词
C-H ARYLATION; N-ALKOXYIMIDOYL BROMIDES; IN-SITU; ASYMMETRIC-SYNTHESIS; VISIBLE-LIGHT; ASCORBIC-ACID; (HETERO)ARENES; PHOTOREDOX; REDUCTION; DONORS;
D O I
10.1021/acs.joc.1c01197
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfonyl oxime ethers undergo facile radical substitutions with various amines to yield the corresponding oxime ethers. An efficient arylation of sulfonyl oxime ethers was accomplished under ambient temperature and metal-free conditions, with a wide range of functional group tolerance. Mechanistic investigations indicate that a phenyl radical is involved in the catalytic cycle.
引用
收藏
页码:12676 / 12682
页数:7
相关论文
共 50 条
  • [21] INSECTICIDAL SUBSTITUTED BIPHENYLMETHYL OXIME ETHERS
    CULLEN, TG
    MANLY, CJ
    CRUICKSHANK, PA
    KELLAR, SM
    ACS SYMPOSIUM SERIES, 1987, 355 : 173 - 188
  • [22] REARRANGEMENT OF OXIME N-ETHERS
    COPE, AC
    HAVEN, AC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) : 4896 - 4903
  • [23] Chemoselective addition of organometallics to oxime ethers
    Tavakol, Hossein
    Zakery, Saedeh
    Heydari, Akbar
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (10) : 1924 - 1927
  • [24] EFFECT OF SIZE OF NONCONJUGATED OXIME MOIETY ON THE KINETICS OF AMINOLYSIS OF OXIME ETHERS
    JAIN, AK
    GUPTA, VK
    KUMAR, A
    REACTION KINETICS AND CATALYSIS LETTERS, 1989, 40 (01): : 125 - 130
  • [25] ERYTHROMYCIN-A OXIME 11,12-CARBONATE AND ITS OXIME ETHERS
    BRAIN, EG
    FORREST, AK
    HUNT, E
    SHILLINGFORD, C
    WILSON, JM
    JOURNAL OF ANTIBIOTICS, 1989, 42 (12): : 1817 - 1822
  • [26] Preparation of cycloalkanone oxime ethers via a free radical acylation approach
    Kim, S
    Kim, N
    Yoon, JY
    Oh, DH
    SYNLETT, 2000, (08) : 1148 - 1150
  • [27] Visible-Light-Driven Photocatalyst-Free Deoxygenative Radical Transformation of Alcohols to Oxime Ethers
    Bao, Wen-Hui
    Wu, Xuesong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3975 - 3980
  • [28] A SIMPLE SYNTHESIS OF SOME NOVEL OXIME ETHERS
    AKCAMUR, Y
    KOLLENZ, G
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1987, 19 (01) : 52 - 56
  • [29] THERMOLYSIS OF OXIME O-ALLYL ETHERS
    ECKERSLEY, A
    ROGERS, NAJ
    TETRAHEDRON LETTERS, 1974, (18) : 1661 - 1664
  • [30] Oxime ethers as structure analogs of clavulanic acid
    Pfaendler, HR
    Meffert, H
    HETEROCYCLES, 1998, 47 (02) : 1013 - 1015