Flavin Catalyzed Oxidations of Sulfides and Amines with Molecular Oxygen

Yasushi Imada,* Hiroki Iida, Satoshi Ono, and Shun-Ichi Murahashi*
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3, Machikaneyama, Toyonaka, Osaka 560-8531, Japan, and Department of Applied Chemistry, Okayama University of Science, 1-1, Ridaicho, Okayama 700-0005, Japan
J. Am. Chem. Soc., 2003, 125 (10), pp 2868–2869
DOI: 10.1021/ja028276p
Publication Date (Web): February 12, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mura@chem.es.osaka-u.ac.jp

Abstract

Abstract Image

Novel biomimetic, aerobic oxidation with an organocatalyst was performed. The oxidations of organic substrates such as sulfides, secondary amines, N-hydroxylamines, and tertiary amines with molecular oxygen (1 atm) or even in air in the presence of 5-ethyl-3-methyllumiflavinium perchlorate catalyst and hydrazine monohydrate in 2,2,2-trifluoroethanol occur highly efficiently to give the corresponding oxidized compounds in excellent yields along with water and molecular nitrogen, which are environmentally benign. The TON of the oxidation of sulfides amounts to 19 000.

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History

  • Published In Issue March 12, 2003
  • Received August 26, 2002

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