Download PDF
Synthesis 2013; 45(19): 2684-2688
DOI: 10.1055/s-0033-1338420
special topic
© Georg Thieme Verlag Stuttgart · New York

Facile Aerobic Photooxidation of Alcohols Using 2-Chloroanthraquinone under Visible Light Irradiation

Yoshiko Shimada
Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan   Fax: +81(58)2308108   Email: itoha@gifu-pu.ac.jp
,
Kasumi Hattori
Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan   Fax: +81(58)2308108   Email: itoha@gifu-pu.ac.jp
,
Norihiro Tada
Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan   Fax: +81(58)2308108   Email: itoha@gifu-pu.ac.jp
,
Tsuyoshi Miura
Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan   Fax: +81(58)2308108   Email: itoha@gifu-pu.ac.jp
,
Akichika Itoh*
Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan   Fax: +81(58)2308108   Email: itoha@gifu-pu.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 08 March 2013

Accepted after revision: 20 March 2013

Publication Date:
16 May 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

A facile photooxidation of alcohols to obtain carboxylic acids and ketones using easily handled 2-chloroanthraquinone as an organocatalyst under visible light irradiation in an air atmosphere is reported. The reaction conditions are mild, such as an air atmosphere and ambient pressure and temperature.

Key words

alcohols - carboxylic acids - 2-chloroanthraquinone - photooxidation - visible light
 

  • References

  • 1 Larock RC. Comprehensive Organic Transformations . 2nd ed. Wiley-VCH; Weinheim: 1999
    Google Scholar

      • For recent examples of oxidation of alcohols to the corresponding carboxylic acids with molecular oxygen, see:
    • 2a Figiel PJ, Sobczak JM, Ziólkowski JJ. Chem. Commun. 2004; 244
    • 2b Ebitani K, Ji H.-B, Mizugaki T, Kaneda K. J. Mol. Catal. A: Chem. 2004; 212: 161
      Crossref
    • 2c Baucherel X, Gonsalvi L, Arends IW. C. E, Ellwood S, Sheldon RA. Adv. Synth. Catal. 2004; 346: 286
      Crossref
    • 2d Matsumura Y, Yamamoto Y, Moriyama N, Furukubo S, Iwasaki F, Onomura O. Tetrahedron Lett. 2003; 45: 8221
    • 2e Uozumi Y, Nakao R. Angew. Chem. Int. Ed. 2003; 42: 194
      Crossref
  • 4 Tada N, Hattori K, Nobuta T, Miura T, Itoh A. Green Chem. 2011; 13: 1669
    Crossref
  • 5 Anastas PT, Warner JC. Green Chemistry, Theory and Practice . Oxford University Press; Oxford: 1998
    Google Scholar
  • 6 2-Chloroanthraquinone absorbs light with wavelengths shorter than 450 nm, and the fluorescent lamp radiates visible light with wavelengths longer than 400 nm. Thus, 2-chloroanthraquinone absorbs light between 400 and 450 nm.