Work

Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups

Year: 2023

Type: article

Abstract: This report describes the reactions between N-heterocyclic carbene copper(I) fluoroalkyl complexes and aryl halides bearing ortho -directing groups. Pyridine, pyrazole, oxazoline, imine, and ester directing groups are shown to dramatically enhance the reactivity of aryl bromides and chlorides with (IPr)Cu I –fluoroalkyl complexes (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; fluoroalkyl = difluoromethyl and pentafluoroethyl) to afford aryl–fluoroalkyl coupling products. This approach is leveraged to achieve the Cu-catalyzed directed fluoroalkylation of a series of aryl bromide substrates.

Source: Organometallics

DOI: 10.1021/acs.organomet.3c00066

Authors: Jonathan R. Hall, Isaac M. Blythe, Liam S. Sharninghausen, Melanie S. Sanford

Institution: University of Michigan

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: Copper Catalyzed Fluorination of Aryl Halides, G2799360258, G4595868749, Metal-Catalyzed Reactions for Organic Synthesis