# Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

**Authors:** Samuel M G Dearman, Xiang Li, Yang Li, Kuldip Singh, Alison M Stuart

PMC · DOI: 10.3762/bjoc.20.157 · Beilstein Journal of Organic Chemistry · 2024-07-29

## TL;DR

A new, efficient method for making hypervalent iodine(V) fluorides using Selectfluor is introduced, offering a milder alternative to traditional harsh reagents.

## Contribution

A mild and efficient procedure using Selectfluor to synthesize hypervalent iodine(V) fluorides with high yields.

## Key findings

- Hypervalent iodine(V) fluorides were prepared in good yields (72–90%) using Selectfluor.
- Bicyclic difluoro(aryl)-λ5-iodane 6 showed greater stability in acetonitrile-d3 compared to chloroform-d1.

## Abstract

The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72–90%). Stability studies revealed that bicyclic difluoro(aryl)-λ5-iodane 6 was much more stable in acetonitrile-d3 than in chloroform-d1, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.

## Linked entities

- **Chemicals:** Selectfluor (PubChem CID 2724933), trifluoromethyl hypofluorite (PubChem CID 78989), bromine trifluoride (PubChem CID 24594), acetonitrile-d3 (PubChem CID 123151), chloroform-d1 (PubChem CID 71583)

## Full-text entities

- **Chemicals:** trifluoromethyl hypofluorite (MESH:C013314), acetonitrile (MESH:C032159), bromine trifluoride (MESH:C507211), Selectfluor (MESH:C408750), chloroform (MESH:D002725), halogen (MESH:D006219), difluoro(aryl)-lambda5-iodane 6 (-)

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## Figures

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## References

32 references — full list in the complete paper: https://tomesphere.com/paper/PMC11301045/full.md

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Source: https://tomesphere.com/paper/PMC11301045