Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone

被引:22
|
作者
Uyanik, Muhammet [1 ]
Sahara, Naoto [1 ]
Ishihara, Kazuaki [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648603, Japan
关键词
Chlorination; Dearomatization; Oxidation; Phenols; Chemoselectivity; Regioselectivity; CATALYTIC ASYMMETRIC DEAROMATIZATION; SODIUM-HYPOCHLORITE; IPSO-CHLORINATION; METHYL-ETHER; PHENOL; HALOGENATION; CONVENIENT; POTASSIUM; CHLORIDE; CARBON;
D O I
10.1002/ejoc.201801063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed a practical and environmentally benign method for the chlorinative dearomatization of arenols using transient electrophilic chlorinating species generated in situ from inexpensive sodium chloride and Oxone as a Cl source and oxidant, respectively, under mild conditions. Moreover, the regioselective chlorination or chlorinative dearomatization of 1-naphthols was also achieved by changing the reaction conditions.
引用
收藏
页码:27 / 31
页数:5
相关论文
共 50 条
  • [1] Chemoselective Oxidative Spiroetherification and Spiroamination of Arenols Using I+/Oxone Catalysis
    Uyanik, Muhammet
    Sahara, Naoto
    Katade, Outa
    Ishihara, Kazuaki
    ORGANIC LETTERS, 2020, 22 (02) : 560 - 564
  • [2] Oxidative Ritter-type Chloroamidation of Alkenes Using NaCl and Oxone
    Kato, Takehiro
    Okada, Yuya
    Fujii, Yuto
    Uyanik, Muhammet
    Ishihara, Kazuaki
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (11) : 2907 - 2910
  • [3] High-Performance Ammonium Hypoiodite/Oxone Catalysis for Enantioselective Oxidative Dearomatization of Arenols
    Uyanik, Muhammet
    Kato, Takehiro
    Sahara, Naoto
    Katade, Outa
    Ishihara, Kazuaki
    ACS CATALYSIS, 2019, 9 (12) : 11619 - 11626
  • [4] Simple and regioselective azidoiodination of alkenes using Oxone®
    Curini, M
    Epifano, F
    Marcotullio, MC
    Rosati, O
    TETRAHEDRON LETTERS, 2002, 43 (07) : 1201 - 1203
  • [5] Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C-H Bonds with NaCl/Oxone at Room Temperature
    Zhao, Mengdi
    Lu, Wenjun
    ORGANIC LETTERS, 2017, 19 (17) : 4560 - 4563
  • [6] Regioselective oxyiodination of aromatic compounds using potassium iodide and Oxone®
    Narender, N
    Srinivasu, P
    Kulkarni, SJ
    Raghavan, KV
    SYNTHETIC COMMUNICATIONS, 2002, 32 (15) : 2319 - 2324
  • [7] Synthesis of Cyclopenta-HBCs and their Regioselective Chlorination During Oxidative Cyclodehydrogenation
    Hall, Thomas B. J.
    Hoggard, Bryce R.
    Larsen, Christopher B.
    Lucas, Nigel T.
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (08) : 1106 - 1110
  • [8] An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and Oxone®
    Narender, N
    Srinivasu, P
    Prasad, MR
    Kulkarni, SJ
    Raghavan, KV
    SYNTHETIC COMMUNICATIONS, 2002, 32 (15) : 2313 - 2318
  • [9] Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone
    Wu, GL
    Liu, Q
    Shen, YL
    Wu, WT
    Wu, LM
    TETRAHEDRON LETTERS, 2005, 46 (35) : 5831 - 5834
  • [10] Oxidative cyclization of alkenols with Oxone using a miniflow reactor
    Yamada, Yoichi M. A.
    Torii, Kaoru
    Uozumi, Yasuhiro
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2009, 5