A bench-stable N-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles

被引:13
作者
Kobayashi, Yusuke [1 ]
Masakado, Sota [2 ]
Murai, Takuya [1 ]
Hamada, Shohei [1 ]
Furuta, Takumi [1 ]
Takemoto, Yoshiji [2 ]
机构
[1] Kyoto Pharmaceut Univ, Dept Pharmaceut Chem, Yamashina Ku, Kyoto 6078414, Japan
[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
关键词
C-H-AMINATION; ALKENES; AZIRIDINATION; BONDS; PHOTOCHEMISTRY; REACTIVITY; INHIBITORS; MECHANISM; OXIDATION; REAGENTS;
D O I
10.1039/d1ob00947h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
ortho-Nitro-substituted N-trifluoroacetyl imino-lambda(3)-iodane is a bench-stable trifluoroacetyl nitrene precursor, in which intra- and intermolecular halogen bonding (XB) plays an important role. Potential synthetic applications of this novel precursor were explored.
引用
收藏
页码:6628 / 6632
页数:5
相关论文
共 56 条
  • [1] A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
    Abazid, Ayham H.
    Nachtsheim, Boris J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (04) : 1479 - 1484
  • [2] Tunable, Chemo- and Site-Selective Nitrene Transfer Reactions through the Rational Design of Silver(I) Catalysts
    Alderson, Juliet M.
    Corbin, Joshua R.
    Schomaker, Jennifer M.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) : 2147 - 2158
  • [3] Picolinate-Directed Arene meta-C-H Amination via FeCl3 Catalysis
    Anugu, Raghunath Reddy
    Munnuri, Sailu
    Falck, John R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) : 5266 - 5271
  • [4] Intermolecular chemo- and regioselective aromatic C-H amination of alkoxyarenes promoted by rhodium nitrenoids
    Arai, Kenta
    Ueda, Yoshihiro
    Morisaki, Kazuhiro
    Furuta, Takumi
    Sasamori, Takahiro
    Tokitoh, Norihiro
    Kawabata, Takeo
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (18) : 2264 - 2267
  • [5] Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions
    Baba, Takafumi
    Takahashi, Shunsuke
    Kambara, Yui
    Yoshimura, Akira
    Nemykin, Victor N.
    Zhdankin, Viktor V.
    Saito, Akio
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (21) : 3860 - 3864
  • [6] Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines
    Bizet, Vincent
    Buglioni, Laura
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5639 - 5642
  • [7] Preparation of 1,1'-Oxy-bis(3,3-bis(trifluoromethyl)-3(1H)-1,2-benziodoxole) and 2-(N-(p-Toluenesulfonyl)imino)iodobenzylmethyl Ether
    Blake, Alexander J.
    Novak, Andrew
    Davies, Madeline
    Robinson, Richard I.
    Woodward, Simon
    [J]. SYNTHETIC COMMUNICATIONS, 2009, 39 (06) : 1065 - 1075
  • [8] N-Heterocycle-Stabilized Iodanes: From Structure to Reactivity
    Boelke, Andreas
    Lork, Enno
    Nachtsheim, Boris J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (70) : 18653 - 18657
  • [9] Secondary bonding as a force dictating structure and solid-state aggregation of the primary nitrene sources (arylsulfonylimino)iodoarenes (ArINSO2Ar')
    Boucher, M
    Macikenas, D
    Ren, T
    Protasiewicz, JD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) : 9366 - 9376
  • [10] Transition-metal-catalyzed aminations and aziridinations of C-H and C=C bonds with iminoiodinanes
    Chang, Joyce Wei Wei
    Ton, Thi My Uyen
    Chan, Philip Wai Hong
    [J]. CHEMICAL RECORD, 2011, 11 (06) : 331 - 357