Synthesis of novel fluorinated building blocks via halofluorination and related reactions

Attila Márió Remete; Tamás T Novák; Melinda Nonn; Matti Haukka; Ferenc Fülöp; Loránd Kiss

doi:10.3762/bjoc.16.208

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

Beilstein J Org Chem. 2020 Oct 16:16:2562-2575. doi: 10.3762/bjoc.16.208. eCollection 2020.

Authors

Attila Márió Remete^{1

2}, Tamás T Novák¹, Melinda Nonn^{1

2

3}, Matti Haukka⁴, Ferenc Fülöp^{1

2

3}, Loránd Kiss^{1

2}

Affiliations

¹ Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
² Interdisciplinary Excellence Centre, Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
³ MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Eötvös u. 6, Hungary.
⁴ Department of Chemistry, University of Jyväskylä, FIN-40014, Jyväskylä, Finland.

Abstract

A study exploring halofluorination and fluoroselenation of some cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor^®. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.

Keywords: fluorine; fluoroselenation; functionalization; halofluorination; stereocontrol.

Grants and funding

We are grateful to the Hungarian Research Foundation (NKFIH No K 119282) for financial support. Fnancial support of the GINOP-2.3.2-15-2016-00038 project is also acknowledged. This research was supported by the EU-funded Hungarian grant EFOP-3.6.1-16-2016-00008. The Ministry of Human Capacities, Hungary (grant 20391-3/2018/FEKUSTRAT) is also acknowledged.