Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Aug 17;59(34):14241-14245.
doi: 10.1002/anie.202004902. Epub 2020 Jul 10.

Iodine Catalysis for C(sp3 )-H Fluorination with a Nucleophilic Fluorine Source

Daniel Bafaluy  1 , Zoritsa Georgieva  1 , Kilian Muñiz  1
Affiliations

Iodine Catalysis for C(sp3 )-H Fluorination with a Nucleophilic Fluorine Source

Daniel Bafaluy et al. Angew Chem Int Ed Engl. .

Abstract

Iodine catalysis was developed for aliphatic fluorination through light-promoted homolytic C-H bond cleavage. The intermediary formation of amidyl radicals enables selective C-H functionalization via carbon-centered radicals. For the subsequent C-F bond formation, previous methods have typically been limited by a requirement for electrophilic fluorine reagents. We here demonstrate that the intermediary instalment of a carbon-iodine bond sets the stage for an umpolung, thereby establishing an unprecedented nucleophilic fluorination pathway.

Keywords: C−H bond cleavage; C−H fluorination; amidyl radicals; halogen catalysis; iodine.

PubMed Disclaimer

References

    1. None
    1. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881-1886;
    1. T. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Chem. Soc. Rev. 2011, 40, 3496-3508;
    1. T. Fujiwara, D. O'Hagan, J. Fluorine Chem. 2014, 167, 16-29;
    1. Y. Zhou, J. Wang, Z. Gu, S. Wang, W. Zhu, J. L. Aceña, V. A. Soloshonok, K. Izawa, H. Liu, Chem. Rev. 2016, 116, 422-518.

LinkOut - more resources