Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air

被引:71
作者
Cheng, Zhen [1 ]
Sun, Pengchao [1 ]
Tang, Ailing [1 ]
Jin, Weiwei [1 ]
Liu, Chenjiang [1 ]
机构
[1] Xinjiang Univ, Key Lab Oil & Gas Fine Chem, Minist Educ & Xinjiang Uygur Autonomous Reg,Sch C, Urumqi Key Lab Green Catalysis & Synth Technol, Urumqi 830046, Peoples R China
基金
中国国家自然科学基金;
关键词
PHOTOREDOX CATALYSIS; SELECTIVE OXIDATION; DIARYL SULFOXIDES; BENZYL SULFOXIDES; AEROBIC OXIDATION; BOND FORMATION; EFFICIENT; OXYGENATION; ACTIVATION; ALKENES;
D O I
10.1021/acs.orglett.9b03192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O-2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.
引用
收藏
页码:8925 / 8929
页数:5
相关论文
共 55 条
  • [1] Backvall J.-E., 2010, MODERN OXIDATION MET
  • [2] TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Arabi, Mehdi Sheikh
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) : 6208 - 6213
  • [3] Visible-Light-Mediated Oxygenation Reactions using Molecular Oxygen
    Bian, Changliang
    Singh, Atul K.
    Niu, Linbin
    Yi, Hong
    Lei, Aiwen
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) : 386 - 396
  • [4] Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
    Cao, Dawei
    Zhang, Yonghong
    Liu, Chenjiang
    Wang, Bin
    Sun, Yadong
    Abdukadera, Ablimit
    Hu, Haiyan
    Liu, Qiang
    [J]. ORGANIC LETTERS, 2016, 18 (09) : 2000 - 2003
  • [5] Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones
    Chawla, Ruchi
    Yadav, Lal Dhar S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4761 - 4766
  • [6] CMPs as Scaffolds for Constructing Porous Catalytic Frameworks: A Built-in Heterogeneous Catalyst with High Activity and Selectivity Based on Nanoporous Metalloporphyrin Polymers
    Chen, Long
    Yang, Yong
    Jiang, Donglin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 9138 - 9143
  • [7] Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling
    Chen, Yiding
    Willis, Michael C.
    [J]. CHEMICAL SCIENCE, 2017, 8 (04) : 3249 - 3253
  • [8] B2pin2-catalyzed oxidative cleavage of a C?C double bond with molecular oxygen
    Cheng, Zhen
    Jin, Weiwei
    Liu, Chenjiang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) : 841 - 845
  • [9] Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant
    Cui, Huanhuan
    Wei, Wei
    Yang, Daoshan
    Zhang, Yulong
    Zhao, Huijuan
    Wang, Leilei
    Wang, Hua
    [J]. GREEN CHEMISTRY, 2017, 19 (15) : 3520 - 3524
  • [10] Halogen-Bonding-Assisted Iodosylbenzene Activation by a Homogenous Iron Catalyst
    de Sousa, David P.
    Wegeberg, Christina
    Vad, Mads Sorensen
    Morup, Steen
    Frandsen, Cathrine
    Donald, William A.
    McKenzie, Christine J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (11) : 3810 - 3820