Selective monofluorination of 1,2- and 1,3-diols was achieved by reaction with DFMBA. The method is applicable for the synthesis of optically-active fluorohydrin derivatives. The Royal Society of Chemistry 2005.
Yoneda, Atsushi,Fukuhara, Tsuyoshi,Hara, Shoji
p. 3589 - 3590
(2007/10/03)
Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro- (m-methylbenzyl)amine
Deoxyfluorination of alcohols was carried out using N,N-diethyl-α, α-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions.