Visible-Light-Driven Photocatalyst-Free Deoxygenative Radical Transformation of Alcohols to Oxime Ethers

被引:18
作者
Bao, Wen-Hui [1 ]
Wu, Xuesong [1 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Bioinorgan Chem & Mat Med, Wuhan 430074, Peoples R China
基金
中国国家自然科学基金;
关键词
ACYLATION APPROACH; CARBOXYLIC-ACIDS; CONVERSION; FENPYROXIMATE; ALKENYLATION; ESTERS;
D O I
10.1021/acs.joc.2c03043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-driven deoxygenative cross-coupling of alcohols with sulfonyl oxime ethers has been developed by using xanthate salts as alcohol-activating groups. Upon convenient generation and direct photoexcitation of xanthate anions, a broad range of alcohols including primary ones can efficiently undergo this transformation to afford diverse oxime ethers and derivatives. This one-pot protocol features mild conditions, broad substrate scope, and late-stage applicability, without the need for any external photocatalysts or electron donor-acceptor complex formation.
引用
收藏
页码:3975 / 3980
页数:6
相关论文
共 54 条
  • [1] Abele E., 2003, KHIM GETEROTSIKL, V39, p3?35
  • [2] Abele E., 2005, Chem. Heterocycl. Comp, V41, P137
  • [3] Determination of Degradation Rate of Acaricide Fenpyroximate in Apple, Citrus, and Grape by HPLC-DAD
    Al-Rahman, Sherif H. Abd
    Almaz, M. M.
    Osama, I. A.
    [J]. FOOD ANALYTICAL METHODS, 2012, 5 (02) : 306 - 311
  • [4] Radical Deoxyfunctionalisation Strategies
    Anwar, Khadijah
    Merkens, Kay
    Aguilar Troyano, Francisco Jose
    Gomez-Suarez, Adrian
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (26)
  • [5] Metal-Involving Synthesis and Reactions of Oximes
    Bolotin, Dmitrii S.
    Bokach, Nadezhda A.
    Demakova, Marina Ya.
    Kukushkin, Vadim Yu.
    [J]. CHEMICAL REVIEWS, 2017, 117 (21) : 13039 - 13122
  • [6] Recent advances in cyclization reactions of unsaturated oxime esters (ethers): synthesis of versatile functionalized nitrogen-containing scaffolds
    Chen, Chen
    Zhao, Jinghui
    Shi, Xiaonan
    Liu, Liying
    Zhu, Yan-Ping
    Sun, Wan
    Zhu, Bolin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (14): : 1948 - 1969
  • [7] Chung WJ, 2002, B KOR CHEM SOC, V23, P1187
  • [8] Metallaphotoredox-enabled deoxygenative arylation of alcohols
    Dong, Zhe
    MacMillan, David W. C.
    [J]. NATURE, 2021, 598 (7881) : 451 - +
  • [9] Cobalt Catalyzed Functionalization of Unactivated Alkenes: Regioselective Reductive C-C Bond Forming Reactions
    Gaspar, Boris
    Carreira, Erick M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (37) : 13214 - 13215
  • [10] Multicomponent radical processes: Synthesis of substituted piperidinones
    Godineau, Edouard
    Landais, Yannick
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12662 - +