Research title: Site-Specific Synthesis of β-Fluorinated γ-Butyrolactams via Decarboxylative Fluorination of β-Carboxyl-γ-Butyrolactams
Institute: Department of Chemistry, Faculty of Science, Mahidol Unniversity
Research background and its significance: Monofluorinated γ‐butyrolactams bearing fluorine atom within functionalized structures are of increasing demand in both academic researches and industrial sections, particularly in pharmaceutical industry. This attributed to the profound effects that the incorporation of fluorine atoms at specific position of cyclic nitrogen‐containing compounds can lead to the improved biological activities. Therefore, the development of efficient and site‐specific stereoselective synthesis of chiral fluorinated γ‐butyrolactams is of considerable importance. Although synthetic methods for the synthesis of α‐fluorinated carbonyl compounds are available, those for selective synthesis of β‐fluorinated carbonyl compounds are still limited.
In this work, the direct and site‐specific synthesis of β‐fluorinated γ‐butyrolactams via AgNO3 mediated decarboxylative fluorination of β‐carboxyl‐γ‐butyrolactams using Selectfluor® as a fluorine source was described. The developed methods should be found useful and applicable to the synthesis of β‐fluorinated γ‐butyrolactams and related fluorinated nitrogen‐containing compounds which are an important class of compounds for organic synthesis and pharmaceutical science.
Scope of research: This work involved the development of new synthetic reactions for the synthesis of β-fluorinated γ-butyrolactams and related fluorinated nitrogen-containing compounds focusing on the decarboxylative fluorination process.
Objective: To develop new synthetic reactions for the synthesis of β-fluorinated γ-butyrolactams and related fluorinated nitrogen-containing compounds based on the decarboxylative fluorination process.
Research grants: Thailand Research Fund (RSA6180025 and IRN58W0005) / the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation / the Office of the Higher Education Commission and Mahidol University under the National Research Universities Initiative / CNRS-PICS Program (PICS6663) / The Franco-Thai Cooperation Program in Higher Education and Research (PHC-Siam 2017) / National Science and Technology Development Agency (NSTDA) (through student scholarship to S. P.).
Stakeholder: Scientific community
Level of collaboration: –
Output/Outcome: Publication / new knowledge / new synthetic reactions for the synthesis of β-fluorinated γ-butyrolactams and related fluorinated nitrogen-containing compounds.
Web link: https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201900685; DOI: 10.1002/ejoc.201900685
Related SDG goal: 9. Industry, Innovation and Infrastructure (9.5 and 9.b)