Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes

被引:37
作者
Amri, Nasser [1 ]
Wirth, Thomas [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, Wales
关键词
EFFICIENT SYNTHESIS; SULFIDES; OXIDATION; CONSTRUCTION; CATALYST; ACCESS; SCAFFOLDS; THIOLS;
D O I
10.1021/acs.joc.1c00860
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides to N-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, and N-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
引用
收藏
页码:15961 / 15972
页数:12
相关论文
共 70 条
  • [1] SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling
    Adenot, Aurelien
    Char, Joelle
    von Wolff, Niklas
    Lefevre, Guillaume
    Anthore-Dalion, Lucile
    Cantat, Thibault
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (86) : 12924 - 12927
  • [2] Recent Advances in the Electrochemical Synthesis of Organosulfur Compounds
    Amri, Nasser
    Wirth, Thomas
    [J]. CHEMICAL RECORD, 2021, 21 (09) : 2526 - 2537
  • [3] Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites
    Amri, Nasser
    Wirth, Thomas
    [J]. SYNLETT, 2020, 31 (19) : 1894 - 1898
  • [4] Automated Electrochemical Selenenylations
    Amri, Nasser
    Wirth, Thomas
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (12): : 1751 - 1761
  • [5] Efficient Flow Electrochemical Alkoxylation of Pyrrolidine-1-carbaldehyde
    Amri, Nasser
    Skilton, Ryan A.
    Guthrie, Duncan
    Wirth, Thomas
    [J]. SYNLETT, 2019, 30 (10) : 1183 - 1186
  • [6] Sulfur imidations: access to sulfimides and sulfoximines
    Bizet, Vincent
    Hendriks, Christine M. M.
    Bolm, Carsten
    [J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (11) : 3378 - 3390
  • [7] Mild, Selective Sulfoxidation with Molybdenum(VI) cis-Dioxo Catalysts
    Cantwell, Kelsey E.
    Fanwick, Phillip E.
    Abu-Omar, Mahdi M.
    [J]. ACS OMEGA, 2017, 2 (05): : 1778 - 1785
  • [8] Electrocatalytic Aziridination of Alkenes Mediated by n-Bu4NI: A Radical Pathway
    Chen, Jie
    Yan, Wei-Qing
    Lam, Chiu Marco
    Zeng, Cheng-Chu
    Hu, Li-Ming
    Little, R. Daniel
    [J]. ORGANIC LETTERS, 2015, 17 (04) : 986 - 989
  • [9] 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
  • [10] General sulfone construction via sulfur dioxide surrogate control
    Chen, Shihao
    Li, Yaping
    Wang, Ming
    Jiang, Xuefeng
    [J]. GREEN CHEMISTRY, 2020, 22 (02) : 322 - 326