Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups.
Organometallics
; 42(7): 543-546, 2023 Apr 10.
Article
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| MEDLINE
| ID: mdl-37841393
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)CuI-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.
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MEDLINE
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Organometallics
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2023
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Article