Flavin catalyzed oxidations of sulfides and amines with molecular oxygen.
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.
Imada
Yasushi
Y
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3, Machikaneyama, Toyonaka, Osaka 560-8531, Japan. mura@chem.es.osaka-u.ac.jp
Iida
Hiroki
H
Ono
Satoshi
S
Murahashi
Shun-Ichi
S
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005415:Flavins / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010105:Oxygenases / Q000737:chemistry / Q000378:metabolism; D013440:Sulfides / Q000737:chemistry*
D000588:Amines; D005415:Flavins; D013440:Sulfides; C001922:lumiflavin; D010105:Oxygenases; C020066:dimethylaniline monooxygenase (N-oxide forming); D010100:Oxygen