Efficient synthesis of thioesters and amides from aldehydes by using an intermolecular radical reaction in water.
The combination of the water-soluble radical initiator, 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044) and the surfactant, cetyltrimethyl-ammonium bromide (CTAB), was found to be the most suitable condition for the effective and direct synthesis of useful active thioesters (pentafluorophenyl thioesters) in water. In addition, the direct amidation of aldehydes was achieved by the addition of the amines to the thioesterification reaction mixture in water.
Nambu
Hisanori
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
Hata
Kayoko
K
Matsugi
Masato
M
Kita
Yasuyuki
Y
D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis*; D000077286:Cetrimonium; D002593:Cetrimonium Compounds; D004952:Esters / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D000577:Amides; D002593:Cetrimonium Compounds; D004952:Esters; D007202:Indicators and Reagents; D014867:Water; D000077286:Cetrimonium