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)


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.

 
  • References

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

    • 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
    • 2c Baucherel X, Gonsalvi L, Arends IW. C. E, Ellwood S, Sheldon RA. Adv. Synth. Catal. 2004; 346: 286
    • 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
  • 4 Tada N, Hattori K, Nobuta T, Miura T, Itoh A. Green Chem. 2011; 13: 1669
  • 5 Anastas PT, Warner JC. Green Chemistry, Theory and Practice . Oxford University Press; Oxford: 1998
  • 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.