Studies on Fluorinative Difunctionalization of Some β-Amino Acid Derivatives and β-Lactams with a Cycloalkene Framework

• studies on the arylfluorination of some β -lactams and β -amino esters were performed • types of fluorinating agents and the palladium catalysts have been investigated • possible synthetic routes on the olefin bond difunctionalizations are presented Studies on the arylfluorination of some β -lactams and β -amino esters with a cyclooctene framework were performed under various experimental conditions with emphasis on the type of the fluorinating agents and the palladium catalysts. The arylfluorinative difunctionalization of cyclooctene-fused β -lactam, performed with phenylboronic acid, in the presence of several electrophilic fluorinating agents [1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate, 1-fluoropyridinium triflate, N -fluorobenzensulfonimide) and palladium catalyst ( bis (dibenzylideneacetone)palladium(0), bis (acetonitrile)dichloropalladium(II), bis (triphenylphosphine)palladium(II) dichloride, palladium(II) chloride], azacyclic ligands, and solvents, gave a separable mixture of five fluorinated and non-fluorinated products. Arylfluorination of cyclooctane- β -amino esters when performed under similar conditions proceeded with full regio- and stereoselective manners affording phenyl-fluorinated compounds. Possible synthetic routes related to the outcome of these types of olefin bond difunctionalizations are also presented.