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Updated: May 21, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper(I)-Initiated Site-Selective β-ζ-C(sp3)-H Bond Fluorination of Ketones, Carboxylic Esters, and Amides by
Jordan Diaz1, Wai Tsun Or1, James Theodore Merrett1
1School of Chemistry, Monash University, Clayton, Victoria 3800, Australia.
Abstract:
A synthetic method that enables the site-selective fluorination at an unactivated C(sp3)-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(sp3)-F bond formation protocol was exemplified by the late-stage functionalization of five natural product and drug molecule derivatives.
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