352-11-4Relevant articles and documents
p-Fluorobenzaldehyde and p-fluorobenzoic acid by oxidation of p-fluorobenzyl derivatives
Conte,Napoli,Gambaretto,Carlini,Bonini
, p. 19 - 23 (1998)
Experiments on the oxidation reactions of p-fluorobenzyl alcohol and chloride were carried out. Several oxidizing agents (manganese dioxide, 30% hydrogen peroxide and hypochlorite solutions at different concentrations) were used, and a mixture of p-fluorobenzaldehyde and p-fluorobenzoic acid in different proportions was obtained. In the case of p-fluorobenzyl chloride, some p-fluorobenzyl alcohol was also found in the reaction mixture. The experimental conditions required to obtain an increase in the yield of the aldehyde or acid were also studied.
One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
, p. 3768 - 3777 (2021/03/01)
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride
Parker, Bernard F.,Hosoya, Hiromu,Arnold, John,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 12825 - 12831 (2019/10/19)
α-Diimine niobium complexes serve as catalysts for deoxygenation of benzyl ethers by silicon tetrachloride (SiCl4) to cleanly give two equivalents of the corresponding benzyl chlorides, where SiCl4 has the dual function of oxygen scavenger and chloride source with the formation of a silyl ether or silica as the only byproduct. The reaction mechanism has two successive trans-etherification steps that are mediated by the niobium catalyst, first forming one equivalent of benzyl chloride along with the corresponding silyl ether intermediate that undergoes the same reaction pathway to give the second equivalent of benzyl chloride and silyl ether.
Synthesis of mono- and difluorobenzyl chlorides by chlorination of mono- and difluorotoluenes with CCl4 and t-BuOCl induced by iron-containing catalysts
Bayguzina, Alfiya R.,Gallyamova, Leysan I.,Khalilov, Leonard M.,Khusnutdinov, Ravil I.
supporting information, (2019/07/19)
Mono- and difluorobenzyl chlorides were synthesized by chlorination of mono- and difluorotoluenes with CCl4?MeOH or t-BuOCl in the presence of iron-containing catalysts.
