Thiocyanate radical mediated dehydration of aldoximes with visible light and air

被引:32
作者
Ban, Yong-Liang [1 ]
Dai, Jian-Ling [1 ]
Jin, Xiao-Ling [1 ]
Zhang, Qing-Bao [1 ]
Liu, Qiang [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
关键词
PHOTOCATALYTIC ANION OXIDATION; PRIMARY AMIDES; ARYL IODIDES; NITRILES; EFFICIENT; CONVERSION; MILD; CYANATION; CATALYST; DIFUNCTIONALIZATION;
D O I
10.1039/c9cc05354a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
引用
收藏
页码:9701 / 9704
页数:4
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  • [1] Adak S, 1997, J BIOL CHEM, V272, P11049
  • [2] Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates
    Anderson, BA
    Bell, EC
    Ginah, FO
    Harn, NK
    Pagh, LM
    Wepsiec, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8224 - 8228
  • [3] Recent Advances in Transition Metal-Catalyzed Hydrogenation of Nitriles
    Bagal, Dattatraya B.
    Bhanage, Bhalchandra M.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) : 883 - 900
  • [4] Indium-mediated facile dehydration and Beckmann rearrangement of grimes
    Barman, DC
    Thakur, AJ
    Prajapati, D
    Sandhu, JS
    [J]. CHEMISTRY LETTERS, 2000, (10) : 1196 - 1197
  • [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 the chemistry of organic thiocyanates
    Castanheiro, Thomas
    Suffert, Jean
    Donnard, Morgan
    Gulea, Mihaela
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 494 - 505
  • [7] Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides
    Cristau, HJ
    Ouali, A
    Spindler, JF
    Taillefer, M
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2483 - 2492
  • [8] Organotellurium catalysis-enabled utilization of molecular oxygen as oxidant for oxidative deoximation reactions under solvent-free conditions
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    Cao, Hongen
    Chen, Chao
    Zhou, Hongwei
    Yu, Lei
    [J]. SCIENCE BULLETIN, 2019, 64 (17) : 1280 - 1284
  • [9] Some recent applications of α-amino nitrile chemistry
    Enders, D
    Shilvock, JP
    [J]. CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) : 359 - 373
  • [10] A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles
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    Yang, Qi
    Xu, Fengshan
    Li, Pixu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10588 - 10592