Application

No.126
Catalytic Aerobic Oxidation of Alcohols
C1944 Chloronitrosyl[N,N'-bis(3,5-di-tert-butylsalicylidene)-1,1,2,2-tetramethylethylenediaminato]ruthenium (IV) (1) 100mg

Compound 1 is a salen-Ru complex which was developed by Katsuki et al. and is activated under visible light irradiation. When used as a catalyst, primary alcohols are selectively oxidized to aldehydes under aerobic conditions.1 When a 1,n-diol, which has both primary and secondary hydroxyl groups, is oxidized in an atmosphere with 20% molecular oxygen, the corresponding lactols can be obtained.1b Compound 1 can even use molecular oxygen at room temperature and therefore is not only an excellent catalyst in terms of atomic efficiency, but is also environmentally friendly.

References

1) Chemoselective aerobic oxidation of primary alcohols
a) A. Miyata, M. Murakami, R. Irie, T. Katsuki, Tetrahedron Lett., 2001, 42, 7067.
b) A. Miyata, M. Furukawa, R. Irie, T. Katsuki, Tetrahedron Lett., 2002, 43, 3481.
c) A. Tashiro, A. Mitsuishi, R. Irie, T. Katsuki, Synlett, 2003, 1868.
d) H. Egami, H. Shimizu, T. Katsuki, Tetrahedron Lett., 2005, 46, 783.
e) T. Katsuki, TCI MAIL, 2004, number 124, 2.
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