4.5 Article

Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 1, Pages 27-31

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801063

Keywords

Chlorination; Dearomatization; Oxidation; Phenols; Chemoselectivity; Regioselectivity

Funding

  1. JSPS. KAKENHI [15H05755, 15H05484, 18H01973]
  2. Program for Leading Graduate Schools: IGER Program in Green Natural Sciences (MEXT)
  3. Grants-in-Aid for Scientific Research [15H05755, 15H05484, 18H01973] Funding Source: KAKEN

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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.

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