- Ionic liquids as media for nucleophilic flurination
-
The use of Room Temperature Ionic Liquids (RTILs) for a variety of halogen exchange (Halex) fluorination processes using alkali metal fluorides is assessed. Whilst fluorination of a range of halogenated substrates is possible in good yield, the utility of RTILs as reusable, inert media for such reactions is limited by the gradual decomposition of the RTIL in the presence of highly basic fluoride ion.
- Murray, Christopher B.,Sandford, Graham,Korn, Stewart R.
-
-
- A useful conversion of alcohols to alkyl fluorides
-
A useful conversion of alcohols to alkyl fluorides via their fluoroformates is introduced. The fluoroformates are obtained in nearly quantitative yield from the alcohols by treatment with COF2 (generated in situ from bis(trichloromethyl) carbonate) in ether with KF as an added acid scavenger. The neat fluoroformates are cleaved to the fluorides by heating at 120-125°C using hexabutylguanidinium fluoride (HBGF) as the catalyst.
- Flosser, David A,Olofson, Roy A
-
p. 4275 - 4279
(2007/10/03)
-
- Cocatalysis by tetravalent tin compounds in phase-transfer catalyzed fluorination of alkyl halides and sulfonates
-
Phase-transfer catalyzed fluorination of alkyl halides or sulfonates is co-catalyzed efficiently by triorganotin halides. The cocatalytic action is due to continuous formation of lipophilic hypervalent triorganodifluorostannate anions, which act as fluori
- Ma?kosza, Mieczys?aw,Bujok, Robert
-
p. 2761 - 2763
(2007/10/03)
-
- Tetrabutylammonium butyldifluorodimethylsilicate and difluorodimethylphenylsilicate, new nucleophilic fluorinating reagents
-
Tetrabutylammonium butyldifluorodimethylsilicate (TAMBS, 1a) and tetrabutylammonium difluorodimethylphenylsilicate (TAMPS, 1b) were conveniently prepared from the corresponding substituted fluorodimethylsilanes and tetrabutylammonium fluoride. Both fluorosilicates 1a, 1b are powerful nucleophilic fluorinating reagents which transform primary or secondary halides, tosylates, or mesylates to the corresponding fluorides in moderate to good yields.
- Kví?ala,Mysík,Paleta
-
p. 547 - 549
(2007/10/03)
-
- Activation of tetrabutylammonium hydrogen difluoride with pyridine: A mild and efficient procedure for nucleophilic fluorination
-
The nucleophilic fluorination of alkyl iodides, bromides and tosylates and of α-bromo- or α-chloroketones is smoothly effected by tetrabutylammonium hydrogen difluoride in the presence of pyridine, in dioxane or THF, with good or satisfying substitution-to-elimination ratio.
- Moughamir, Khadija,Atmani, Aziz,Mestdagh, Helene,Rolando, Christian,Francesch, Charlette
-
p. 7305 - 7306
(2007/10/03)
-
- Et3n .2Hf, a new convenient reagent for nucleophilic fluorine displacement reactions
-
Syntheses of fluoro compounds by nucleophilic substitution of bromides or methane sulfonates using Et3N .2HF as the reagent are reported. The formation of undesired elimination side products is limited. The synthesis of this new fluorinating reagent is also reported.
- Giudicelli,Pica,Veyron
-
p. 6527 - 6530
(2007/10/02)
-
- Synthesis and Enantioselective Fluorodehydroxylation Reactions of (S)-2-(Methoxymethyl)pyrrolidin-1-ylsulphur Trifluoride, the First Homochiral Aminofluorosulphurane
-
(S)-2-(Methoxymethyl)pyrrolidin-1-ylsulphur trifluoride (7), the first homochiral aminofluorosulphurane and one of the most stable aminofluorosulphuranes yet reported, has been prepared, and has been shown to be an effective enantioselective fluorohydroxylating agent.
- Hann, Gerald L.,Sampson, Paul
-
p. 1650 - 1651
(2007/10/02)
-