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Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

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)2 and KHF2 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.

SUBMITTER: Dorel R 

PROVIDER: S-EPMC7266656 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Dorel Ruth R   Boehm Philip P   Schwinger Daniel P DP   Hartwig John F JF  

Chemistry (Weinheim an der Bergstrasse, Germany) 20200128 8

A method for the nucleophilic fluorination of heptamethyl aryl trisiloxanes to form fluoroarenes is reported. The reaction proceeds in the presence of Cu(OTf)<sub>2</sub> and KHF<sub>2</sub> 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-  ...[more]

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