Cyano migration-mediated radical-polar crossover cyclopropanation

被引:4
作者
Wang, Ziqiang [1 ,2 ,3 ]
Chen, Yasu [2 ,3 ]
Li, Jie [1 ]
Zhu, Chen [1 ,2 ,3 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Shanghai Jiao Tong Univ, Zhangjiang Inst Adv Study, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China
[3] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
cyclopropanation; cyano migration; radical-polar crossover; radical reactions; DIFUNCTIONALIZATION; STRATEGY; ALKENES;
D O I
10.1007/s11426-024-2172-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a novel cyano migration-mediated radical-polar crossover process, whereby both the sulfonylcyanation of aliphatic alkenes and the formation of cyclopropanes are concurrently achieved. This transformation yields a diverse array of multi-substituted cyclopropanes under mild photocatalytic conditions. Mechanistic studies elucidate that the reaction proceeds via intramolecular nucleophilic substitution, leading to the formation of the cyclopropane derivatives.
引用
收藏
页码:241 / 248
页数:8
相关论文
共 39 条
  • [1] Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer
    Allen, Anthony R.
    Noten, Efrey A.
    Stephenson, Corey R. J.
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 2695 - 2751
  • [2] A Stereoconvergent Cyclopropanation Reaction of Styrenes
    del Hoyo, Ana M.
    Herraiz, Ana G.
    Suero, Marcos G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (06) : 1610 - 1613
  • [3] Cyclopropanation of unactivated alkenes with non-stabilized iron carbenes
    DeMuynck, Bethany M.
    Zhang, Lumin
    Ralph, Emma K.
    Nagib, David A.
    [J]. CHEM, 2024, 10 (03): : 1015 - 1027
  • [4] Direct Deaminative Functionalization
    Dherange, Balu D.
    Yuan, Mingbin
    Kelly, Christopher B.
    Reiher, Christopher A.
    Grosanu, Cristina
    Berger, Kathleen J.
    Gutierrez, Osvaldo
    Levin, Mark D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (01) : 17 - 24
  • [5] DiRocco D., 2014, Electrochemical Series of Photocatalysts and Commin Organic Compounds
  • [6] Synthesis of cyclopropane containing natural products
    Donaldson, WA
    [J]. TETRAHEDRON, 2001, 57 (41) : 8589 - 8627
  • [7] Recent developments on 1,2-difunctionalization and hydrofunctionalization of unactivated alkenes and alkynes involving C-S bond formation
    Dong, Bo
    Shen, Jian
    Xie, Lan-Gui
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1322 - 1345
  • [8] Cyclopropanation Strategies in Recent Total Syntheses
    Ebner, Christian
    Carreira, Erick M.
    [J]. CHEMICAL REVIEWS, 2017, 117 (18) : 11651 - 11679
  • [9] Intermolecular Organophotocatalytic Cyclopropanation of Unactivated Olefins
    Fischer, David M.
    Lindner, Henry
    Amberg, Willi M.
    Carreira, Erick M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (02) : 774 - 780
  • [10] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT)
    GOLOLOBOV, YG
    NESMEYANOV, AN
    LYSENKO, VP
    BOLDESKUL, IE
    [J]. TETRAHEDRON, 1987, 43 (12) : 2609 - 2651