# Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

**Authors:** Alexander S Hampton, David R W Hodgson, Graham McDougald, Linhua Wang, Graham Sandford

PMC · DOI: 10.3762/bjoc.20.41 · Beilstein Journal of Organic Chemistry · 2024-02-28

## TL;DR

This paper describes a new method to synthesize difluoro compounds using fluorine gas and quinuclidine.

## Contribution

A novel synthetic approach using fluorine gas and quinuclidine to produce 2,2-difluoro-1,3-dicarbonyl derivatives is introduced.

## Key findings

- 1,3-diketones and 1,3-ketoester derivatives react with fluorine to form 2,2-difluoro-1,3-dicarbonyl derivatives.
- Quinuclidine generates a fluoride ion and an electrophilic N–F agent that facilitate the reaction.

## Abstract

Solutions of 1,3-diketones and 1,3-ketoester derivatives react with fluorine to give the corresponding 2,2-difluoro-1,3-dicarbonyl derivatives in the presence of quinuclidine. Quinuclidine reacts with fluorine in situ to generate a fluoride ion that facilitates limiting enolization processes, and an electrophilic N–F fluorinating agent that is reactive towards neutral enol species.

## Linked entities

- **Chemicals:** fluorine (PubChem CID 24524), quinuclidine (PubChem CID 7527)

## Full-text entities

- **Chemicals:** fluoride (MESH:D005459), Quinuclidine (MESH:D011812), 1,3-diketones (-), fluorine (MESH:D005461)

## Full text

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## Figures

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## References

61 references — full list in the complete paper: https://tomesphere.com/paper/PMC10910478/full.md

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Source: https://tomesphere.com/paper/PMC10910478