Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex

Baunis, Haralds; Pieber, Bartholomäus

Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex

Baunis H, Pieber B. 2023. Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex. European Journal of Organic Chemistry. 26(42), e202300769.

Download

2023_EurJOrgChem_Baunis.pdf 3.28 MB [Published Version]

DOI

10.1002/ejoc.202300769

Journal Article | Published | English

Scopus indexed

Author

Baunis, Haralds^ISTA; Pieber, Bartholomäus^ISTA

Department

Pieber Group

Abstract

We present a photon- and metal-free approach for the radical fluorination of aliphatic oxalate-activated alcohols. The method relies on the spontaneous generation of the N-(chloromethyl)triethylenediamine radical dication, a potent single electron oxidant, from Selectfluor and 4-(dimethylamino)pyridine. The protocol is easily scalable and provides the desired fluorinated products within only a few minutes reaction time.

Publishing Year

2023

Date Published

2023-11-07

Journal Title

European Journal of Organic Chemistry

Publisher

Wiley

Acknowledgement

We gratefully acknowledge the Max-Planck Society and the Institute of Science and Technology Austria (ISTA) for generous financial support. We also thank the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence Strategy – EXC 2008 – 390540038 – UniSysCat for funding. B.P. thanks the Boehringer Ingelheim Foundation for funding through the Plus 3 Perspectives Programme.

Volume

Issue

Article Number

e202300769

ISSN

1434-193X

eISSN

1099-0690

IST-REx-ID

14409

Cite this

Baunis H, Pieber B. Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex. European Journal of Organic Chemistry. 2023;26(42). doi:10.1002/ejoc.202300769

Baunis, H., & Pieber, B. (2023). Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex. European Journal of Organic Chemistry. Wiley. https://doi.org/10.1002/ejoc.202300769

Baunis, Haralds, and Bartholomäus Pieber. “Formal Radical Deoxyfluorination of Oxalate-Activated Alcohols Triggered by the Selectfluor-DMAP Charge-Transfer Complex.” European Journal of Organic Chemistry. Wiley, 2023. https://doi.org/10.1002/ejoc.202300769.

H. Baunis and B. Pieber, “Formal radical deoxyfluorination of oxalate-activated alcohols triggered by the selectfluor-DMAP charge-transfer complex,” European Journal of Organic Chemistry, vol. 26, no. 42. Wiley, 2023.

Baunis, Haralds, and Bartholomäus Pieber. “Formal Radical Deoxyfluorination of Oxalate-Activated Alcohols Triggered by the Selectfluor-DMAP Charge-Transfer Complex.” European Journal of Organic Chemistry, vol. 26, no. 42, e202300769, Wiley, 2023, doi:10.1002/ejoc.202300769.

All files available under the following license(s):

Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0):