158388-60-4Relevant academic research and scientific papers
Biomimetic reductive amination of fluoro aldehydes and ketones via [1,3]-proton shift reaction. Scope and limitations
Ono, Taizo,Kukhar, Valery P.,Soloshonok, Vadim A.
, p. 6563 - 6569 (2007/10/03)
A systematic study of azomethine-azomethine isomerizations of the N-benzylimines 2, derived from fluorinated aldehydes or ketones and benzylamine, has been made. The results reveal that, in sharp contrast to hydrocarbon analogs, fluorinated imines of 2 in triethylamine solution undergo isomerizations to give the corresponding N-benzylidene derivatives 5 (for 5/2 K > 32) in good isolated yields. The rates of the isomerizations depend on the starting imine structures and increase in the following order: aryl perfluoroalkyl ketimine 2m, per(poly)fluoroalkyl aldimine 2a,d-g, perfluoroaryl aldimine 2h, alkyl perfluoroalkyl ketimine 2i,j. The presence of chlorine or bromine atoms in the α-position to the C=N double bond of the starting imine favors a dehydrohalogenation reaction, giving rise to unsaturated products 6-9. The azomethine-azomethine isomerization was studied and proven to proceed essentially (>98%) intramolecularly with isotope exchange experiments. High chemical yields, the simplicity of the experimental procedure, and the low cost of all reagents employed make this biomimetic transamination of fluorocarbonyl compounds a practical method for preparing fluorine-containing amines of biological interest.
A practical route to fluoroalkyl- and fluoroarylamines by base-catalyzed [1,3]-proton shift reaction
Soloshonok,Soloshonok, Vadim A.,Kirilenko,Kirilenko, Alexander G.,Kukhar,Kukhar, Valery P.,Resnati,Resnati, Giuseppe
, p. 3119 - 3122 (2007/10/02)
The base-catalyzed [1,3]-proton shift reaction is shown to be an efficient general approach to fluoroalkyl and fluoroaryl amines starting from appropriate carbonyl compounds and benzylamine.
