35564-19-3Relevant articles and documents
Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride
Dorel, Ruth,Boehm, Philip,Schwinger, Daniel P.,Hartwig, John F.
supporting information, p. 1759 - 1762 (2020/02/05)
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.
Anhydrous tetrabutylammonium fluoride
Sun, Haoran,DiMagno, Stephen G.
, p. 2050 - 2051 (2007/10/03)
Tetrabutylammonium fluoride (TBAF) is prepared at low temperature by nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide. Adventitious water is scavenged during this synthesis by the generated hexacyanobenzene, which readily adds water under basic conditions. Contrary to expectations, TBAF is stable to Hofmann elimination in polar aprotic solvents under anhydrous conditions. Added hydroxylic solvents are shown to catalyze the decomposition of TBAF and to catalyze proton exchange with DMSO. The synthetic utility of this salt is described briefly. Copyright