Copper(I)-Initiated Site-Selective β–ζ-C(sp<sup>3</sup>)–H Bond Fluorination of Ketones, Carboxylic Esters, and Amides by Selectfluor
A synthetic method that enables the site-selective fluorination at an unactivated C(sp<sup>3</sup>)-H bond located two to six C-C bond distances from the C═O group in ketones, carboxylic esters, and amides by Selectfluor [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] aided by a copper(I) salt is described. The site selectivity of the C(sp<sup>3</sup>)-F bond formation protocol was exemplified by the late-stage functionalization of five natural product and drug molecule derivatives.
Authors
- Philip Wai Hong Chan (ORCID: https://orcid.org/0000-0002-8786-6143)
- James Theodore Merrett
- Bo Xia (ORCID: https://orcid.org/0000-0002-7791-2636)
- Jordan Diaz
- Wai Tsun Or
Institutions
- Australian Regenerative Medicine Institute (AU)
- Jiyang College of Zhejiang A&F University (CN)
- Monash University (AU)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c00609
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- Australian Research Council