Copper(I)-InitiatedSite-Selective β–ζ-C(sp<sup>3</sup>)–H BondFluorination 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.

Publication Details

Journal
Figshare
Published
2025-03-21
DOI
https://doi.org/10.1021/acs.orglett.5c00609.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Copper(I)-InitiatedSite-Selective β–ζ-C(sp3)–H BondFluorination of Ketones, Carboxylic Esters,and Amides by Selectfluor

Figshare
Fluorine in Organic Chemistry
article

Copper(I)-InitiatedSite-Selective β–ζ-C(sp3)–H BondFluorination of Ketones, Carboxylic Esters,and Amides by Selectfluor

article en

Abstract

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.

Figshare
Openalex Percentile: Top 65%
Fluorine in Organic Chemistry
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Copper(I)-InitiatedSite-Selective β–ζ-C(sp<sup>3</sup>)–H BondFluorination of Ketones, Carboxylic Esters,and Amides by Selectfluor · Figshare (2025) | TGRS Research Map | TGRS