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Saturated F2-rings from Alkenes

17 September 2024, Version 2
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A general method to convert simple exocyclic alkenes (no Ar-substituents) into saturated F2-rings has been developed. The reaction involves the IIII-reagent C6F5I(OAc)2 (F5-PIDA). The reaction efficiently works on a mg-, g-, and even multigram scale.

Keywords

ring-expansion
alkene
drug modification
natural product
fluorine

Supplementary materials

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supporting information
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experimental details, characterization of compounds
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Version History

Sep 17, 2024 Version 2

Version Notes

The manuscript has been revised to more accurately reflect the background of the study. Additionally, the references have been updated accordingly.

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-0wf3l-v2
D O I: 10.26434/chemrxiv-2024-0wf3l-v2 [opens in a new tab]

Funding

National Natural Science Foundation of China
22371311
Guangdong Provincial Key Laboratory of Construction Foundation
2023B1212060022

Author’s competing interest statement

VS, IL, PM are employees of a chemical supplier Enamine. C6F5I(OAc)2 (F5-PIDA) is commercially available at Enamine under code EN300-46874786.

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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