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DOI: 10.1055/a-2609-9601
Fluorinative Difunctionalization of a Cyclooctene-Fused β-Lactam and Cyclooctene-Fused β-Amino Esters
The authors gratefully acknowledge financial support from the Nemzeti Kutatási Fejlesztési és Innovációs Hivatal (NKFIH/OTKA) (National Research, Development and Innovation Office) of Hungary (FK 145394 and K 142266). We are also grateful for the support provided by the European Union (Project no. RRF-2.3.1-21-2022-00015). This work was supported by the János Bolyai Research Scholarship to M.N. from Magyar Tudományos Akadémia (Hungarian Academy of Sciences).

Abstract
The synthesis of novel arylfluorinated cyclic β-amino acid and β-lactam derivatives is accomplished. Studies on the Pd-catalyzed arylfluorination of the double bond of a cyclooctene-fused azetidine-2-one and various β-amino esters are performed under versatile experimental conditions. The arylfluorinative difunctionalization of a cyclooctene-fused β-lactam, performed with phenylboronic acid in the presence of Selectfluor, palladium diacetate, azacyclic ligands and different solvents, gave a separable mixture of fluorinated and non-fluorinated products. In contrast, arylfluorination of cyclooctane-β-amino esters, performed under similar conditions, proceed with full regio- and stereoselective control, leading to single phenyl-fluorinated products. Possible synthetic pathways for these transformations are also proposed.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2609-9601.
- Supporting Information
Publication History
Received: 11 April 2025
Accepted after revision: 14 May 2025
Accepted Manuscript online:
14 May 2025
Article published online:
11 June 2025
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