27238-93-3Relevant articles and documents
Trimethylsilyl Bis(trifluoromethanesulfonyl)amide as an Effective Catalyst for the Friedel-Crafts Alkylation Reaction
Ishii, Akihiro,Kotera, Osamu,Saeki, Takao,Mikami, Koichi
, p. 1145 - 1146 (1997)
Trimethylsilyl bis(trifluoromethanesulfonyl)amide is shown to be an effective catalyst not only for the Friedel-Crafts alkylation of an aromatic compound but also for allylation or bis-allylation of carbonyl derivatives.
Nickel-Catalyzed Chain-Walking Cross-Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction
Brzozowska, Aleksandra,Kumar, Gadde Sathish,Nikolaienko, Pavlo,Peshkov, Anatoly,Rueping, Magnus,Zhu, Chen
supporting information, p. 6513 - 6519 (2020/03/19)
The first electrochemical approach for nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivity under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale, thus indicating potential for industrial application. Mechanistic investigation suggested the formation of a nickel hydride in the electroreductive chain-walking arylation, which led to the development of a new nickel-catalyzed hydroarylation of styrenes to provide a series of 1,1-diaryl alkanes in good yields under mild reaction conditions.
Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol
Richmond, Edward,Yi, Jing,Vukovi?, Vuk D.,Sajadi, Fatima,Rowley, Christopher N.,Moran, Joseph
, p. 6411 - 6416 (2018/08/12)
Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor-acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Br?nsted acid in hexafluoroisopropanol (HFIP) solvent, constituting a rare example where such cyclopropanes engage in intermolecular C-C bond formation. Branched products are obtained when electron-rich arylcyclopropanes react with a broad scope of arene nucleophiles in accord with a simple SN1-type ring-opening mechanism. In contrast, linear products are obtained when cyclopropylketones react with electron-rich arene nucleophiles. In the latter case, mechanistic experiments and DFT-calculations support a homo-conjugate addition pathway.
