Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Chemistry

Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720, USA.

Published: February 2020

AI Article Synopsis

  • - A new method for adding fluorine to heptamethyl aryl trisiloxanes is introduced, resulting in fluoroarenes.
  • - This reaction uses Cu(OTf) and KHF as fluoride supplies and works well under mild conditions with various heptamethyltrisiloxyarenes.
  • - By combining this fluorination method with aryl C-H bond silylation, researchers achieved selective fluorination of non-reactive arenes based on steric factors using a two-step process.

Article Abstract

A method for the nucleophilic fluorination of heptamethyl aryl trisiloxanes to form fluoroarenes is reported. The reaction proceeds in the presence of Cu(OTf) and KHF as the fluoride source under mild conditions for a broad range of heptamethyltrisiloxyarenes with high functional group tolerance. The combination of this method with the silylation of aryl C-H bonds enables the regioselective fluorination of non-activated arenes controlled by steric effects following a two-step protocol.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7266656PMC
http://dx.doi.org/10.1002/chem.201905040DOI Listing

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