75197-98-7Relevant academic research and scientific papers
Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion
Lu, Deng-Fu,Zhu, Cheng-Liang,Sears, Jeffrey D.,Xu, Hao
supporting information, p. 11360 - 11367 (2016/10/12)
We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
SELECTIVE REDUCTION OF β-FLUOROAZIDES TO β-FLUOROAMINES
Hamman, S.,Beguin, C.G.
, p. 191 - 196 (2007/10/02)
Three methods were tested to reduce chemoselectively β-fluoroazides into β-fluoroamines : catalytic hydrogenation, catalytic transfer hydrogenation, and reduction with triphenyl phosphine.The last was the best.
Ring Opening of Aziridines by Different Fluorinating Reagents: Three Synthetic Routes to α,β-Fluoro Amines with Different Stereochemical Pathways
Alvernhe, Gerald M.,Ennakoua, Christine M.,Lacombe, Sylvie M.,Laurent, Andre J.
, p. 4938 - 4948 (2007/10/02)
The syntheses of α,β-fluoro amines from the reaction of secondary aziridines with either Olah's reagent (HF, pyridine) or anhydrous hydrogen fluoride and of N-activated aziridines with partially neutralized Olah's reagent (NR3-nHF) are reported.The stereo
Preparation of Fluoro Amines by the Reaction of Aziridines with Hydrogen Fluoride in Pyridine Solution
Wade, Tamsir N.
, p. 5328 - 5333 (2007/10/02)
Hydrogen fluoride combines regiospecifically with aziridines (1) to give 2-fluoro amines (6) in good yields.Fluorine attack is in all cases completely directed to the most substituted ring carbon or to the benzylic carbon.The results, for benzylic aziridi
