A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds

26 April 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The site-selective palladium-catalyzed three-component coupling of unactivated alkenyl carbonyl compounds, aryl- or alkenylboronic acids, and N-fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary is proposed to facilitate challenging C(sp3)–F reductive elimination from a Pd(IV) intermediate to afford 1,2-carbofluorination products in good yields and with high regioselectivity.

Keywords

palladium
alkene functionalization
fluorination
cross-coupling
directing group

Supplementary materials

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Description
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Supporting Info
Description
experimental procedures, characterization data for new compounds, copies of NMR spectra, and X-ray crystal structure data
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CIF_S-3
Description
crystallographic information file for compound S-3
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