Copper‐Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride | Zendy

Dorel Ruth | Zendy; Boehm Philip | Zendy; Schwinger Daniel P. | Zendy; Hartwig John F. | Zendy

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Copper‐Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride

Author(s) -

Dorel Ruth,

Boehm Philip,

Schwinger Daniel P.,

Hartwig John F.

Publication year - 2020

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201905040

Subject(s) - nucleophile , steric effects , aryl , regioselectivity , fluoride , chemistry , silylation , copper , functional group , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , alkyl , polymer

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 KHF 2 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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