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
  • [31] IRON-PORPHYRIN AND MANGANESE-PORPHYRIN CATALYZED AZIRIDINATION OF ALKENES BY TOSYL-IMINOIODOBENZENE AND ACYL-IMINOIODOBENZENE
    MANSUY, D
    MAHY, JP
    DUREAULT, A
    BEDI, G
    BATTIONI, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (17) : 1161 - 1163
  • [32] PHOTO-IRRADIATION-PROMOTED AMINOETHERIFICATION OF GLYCALS WITH N-ACYLIMINOIODINANE AND ALCOHOLS
    Masakado, Sota
    Kobayashi, Yusuke
    Takemoto, Yoshiji
    [J]. HETEROCYCLES, 2020, 101 (02) : 453 - 460
  • [33] Photo-Induced Aziridination of Alkenes with N-Sulfonyliminoiodinanes
    Masakado, Sota
    Kobayashi, Yusuke
    Takemoto, Yoshiji
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (06) : 688 - 690
  • [34] Generation of nitrene by the photolysis of N-substituted iminodibenzothiophene
    Morita, Hiroyuki
    Tatami, Atsushi
    Maeda, Tetsuo
    Kim, Lyung Ju
    Kawashima, Wataru
    Yoshimura, Toshiaki
    Abe, Hitoshi
    Akasaka, Takeshi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) : 7159 - 7163
  • [35] Copper-Mediated Perfluoroalkylation of Heteroaryl Bromides with (phen)CuRF
    Mormino, Michael G.
    Fier, Patrick S.
    Hartwig, John F.
    [J]. ORGANIC LETTERS, 2014, 16 (06) : 1744 - 1747
  • [36] A Practical Approach for the Oxidation of Unactivated Csp3-H Bonds with o-Nitro(diacetoxyiodo)benzene as an Efficient Hypervalent Iodine(III)-Based Oxidizing Agent
    Moteki, Shin A.
    Selvakumar, Sermadurai
    Zhang, Tiexin
    Usui, Asuka
    Maruoka, Keiji
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (09) : 932 - 935
  • [37] Hypervalent iodine compounds derived from o-nitroiodobenzene and related compounds: syntheses and structures
    Nikiforov, VA
    Karavan, VS
    Miltsov, SA
    Selivanov, SI
    Kolehmainen, E
    Wegelius, E
    Nissinen, M
    [J]. ARKIVOC, 2003, : 191 - 200
  • [38] BASE-CATALYZED CYCLIZATION OF N-PROPARGYLAMIDES TO OXAZOLES
    NILSSON, BM
    HACKSELL, U
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (02) : 269 - 275
  • [39] Transition Metal-Catalyzed C-H Amination: Scope, Mechanism, and Applications
    Park, Yoonsu
    Kim, Youyoung
    Chang, Sukbok
    [J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9247 - 9301
  • [40] Dirhodium-catalyzed C-H arene amination using hydroxylamines
    Paudyal, Mahesh P.
    Adebesin, Adeniyi Michael
    Burt, Scott R.
    Ess, Daniel H.
    Ma, Zhiwei
    Kurti, Laszlo
    Falck, John R.
    [J]. SCIENCE, 2016, 353 (6304) : 1144 - 1147