Can t-BuOK be a good nucleophile? An ion-pairing answer. Cleavage of aryl ethers in their cationic iron complexes

Abstract

Abstractdendron obtained when the cleavage reaction of the complexes of aryl ethers is carried out in the presence of allyl bromide. During this reaction that is carried out without addition of a salt, it is the in situ formation of KBr during the three deprotonation-allylation sequences that further facilitates the crucial aryl ether cleavage at low temperature.

The Inheritance Angle: A Determinant for the Number of Members in the Substituted Cucurbit[n]uril Family

“…Precedence for t-BuOK as a nucleophile can be found in the report of a nucleophilic attack for an organometallic aryl ether cleavage. 30 Support for the unusual cyclobutene 6 was found in the 1 H and 13 C NMR spectra, especially for the resonances of the olefinic group protons, which were found at δ 7.04 and 142.0 ppm, respectively. Moreover, hydrogenation gave the cyclobutane 4 where the methylene resonances occurred at δ 2.63 and 30.8 ppm, respectively.…”

“…Here the traditional non-nucleophilic base switched roles to act as a nucleophile, hence the source of the O in the furan. Precedence for t -BuOK as a nucleophile can be found in the report of a nucleophilic attack for an organometallic aryl ether cleavage …”

Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes

“…t-BuOK is a strong electron donor and is able to form charge-transfer complexes in which there is electron transfer and reduction of certain substrates; for example: Ph 3 CCl 47-49 and ferrocene derivatives. 50 That is, t-BuOK often acts as a reducing agent. The electrocatalytic experiments have been performed using [(bpy)FeCl 3 ] as a catalyst and R F I as a substrate.…”