Interception of Radicals by Molecular Oxygen and Diazo Compounds: Direct Synthesis of Oxalate Esters Using Visible-Light Catalysis

被引:20
作者
Ma, Meihua [1 ]
Hao, Weiwei [1 ]
Ma, Liang [1 ]
Zheng, Yonggao [1 ]
Lian, Pengcheng [1 ]
Wan, Xiaobing [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
关键词
ASCORBIC-ACID DERIVATIVES; ALPHA-BROMO KETONES; PHOTOREDOX CATALYSIS; AEROBIC OXIDATION; QUATERNARY CARBONS; MEDIATED OXIDATION; DIMETHYL OXALATE; ALKYL; PHOTOCATALYSIS; CARBONYLATION;
D O I
10.1021/acs.orglett.8b02487
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of oxalate esters through a radical process, rather than the traditional ionic reaction, has been well developed in which the radicals induced by visible light are trapped by molecular oxygen and diazo compounds under room temperature. This reaction is operationally simple, mild, and shows broad substrate scopes in alpha-bromo ketones and diazo compounds.
引用
收藏
页码:5799 / 5802
页数:4
相关论文
共 100 条
  • [1] Palladium catalyzed oxidative carbonylation of alcohols: effects of diphosphine ligands
    Amadio, Emanuele
    Freixa, Zoraida
    van Leeuwen, Piet W. N. M.
    Toniolo, Luigi
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (05) : 2856 - 2864
  • [2] Catalytic Properties of [Pd(COOMe)nX2-n(PPh3)2] (n=0, 1, 2; X = Cl, NO2, ONO2, OAc and OTs) in the Oxidative Carbonylation of MeOH
    Amadio, Emanuele
    Cavinato, Gianni
    Dolmella, Alessandro
    Toniolo, Luigi
    [J]. INORGANIC CHEMISTRY, 2010, 49 (08) : 3721 - 3729
  • [3] LED lighting as a simple, inexpensive, and sustainable alternative for Wolff rearrangements
    Bernardim, Barbara
    Hardman-Baldwin, Andrea M.
    Burtoloso, Antonio C. B.
    [J]. RSC ADVANCES, 2015, 5 (18): : 13311 - 13314
  • [4] Functionalized analogues of 5,8,10-trideazafolate as potential inhibitors of GAR Tfase or AICAR Tfase
    Boger, DL
    Haynes, NE
    Warren, MS
    Gooljarsingh, LT
    Ramcharan, J
    Kitos, PA
    Benkovic, SJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (09) : 1831 - 1838
  • [5] ELECTRON-SPIN-RESONANCE STUDIES ON CARBOXYLIC ESTERS .9. SPIN-DENSITY DISTRIBUTION IN DIALKYL OXALATE RADICAL-ANIONS
    BRIX, P
    HELLING, D
    VOSS, J
    [J]. MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (04) : 324 - 326
  • [6] Synthesis of carbon-13 labeled oxalates exhibiting extended nuclear singlet state lifetimes
    Brown, Lynda J.
    Pileio, Giuseppe
    Levitt, Malcolm H.
    Brown, Richard C. D.
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2017, 60 (02) : 135 - 139
  • [7] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b] indoles from aniline-tethered alkylidenecyclopropanes with alkynes
    Cao, Bo
    Wei, Yin
    Shi, Min
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (23) : 2870 - 2873
  • [8] Oxidative carbonylation of ethene catalyzed by Pd(II)-PPh3 complexes in MeOH using benzoquinone as stoichiometric oxidant
    Cavinato, Gianni
    Facchetti, Sarah
    Toniolo, Luigi
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 352 : 63 - 69
  • [9] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1911 - 1923
  • [10] Photoinduced hydroxylperfluoroalkylation of styrenes
    Chen, Tongbi
    Guo, Yong
    Sun, Ke
    Wu, Li-Zhu
    Liu, Wen-Qiang
    Liu, Chao
    Huang, Yangen
    Chen, Qing-Yun
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 1045 - 1048