Studies on fluorinative difunctionalization of some β-amino acid derivatives and β-lactams with a cycloalkene framework

Novák, Tamás T. and Semghouli, Anas and Holczbauer, Tamás and Sulyok-Eiler, Máté and Szabó, Pál T. and Nonn, Melinda and Turczel, Gábor and Fustero, Santos and Hornyánszky, Gábor and Han, Jianlin and Kiss, Loránd (2026) Studies on fluorinative difunctionalization of some β-amino acid derivatives and β-lactams with a cycloalkene framework. JOURNAL OF MOLECULAR STRUCTURE, 1368. No. 146250. ISSN 0022-2860

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Abstract

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.

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