He, Tao; Klare, Hendrik F. T.; Oestreich, Martin published their research in ACS Catalysis in 2021. The article was titled 《Silylium-Ion Regeneration by Protodesilylation Enables Friedel-Crafts Alkylation with Less Isomerization and No Defunctionalization》.Recommanded Product: 622-95-7 The article contains the following contents:
An improved protocol for the Friedel-Crafts alkylation of benzene as well as its methylated and halogenated derivatives with alkyl and benzyl bromides is reported. The reaction is promoted by a counteranion-stabilized silylium ion in the presence of stoichiometric amounts of a simple phenyl-substituted tetraorganosilane. This additive functions as a proton scavenger, regenerating the catalytically active silylium ion through protonation (protodesilylation) by the Wheland intermediate. It is a productive “”proton-into-silylium ion”” generator. The higher proton affinity of silylated compared with alkylated arenes results in fast proton transfer from the Bronsted acidic Wheland intermediate to the ipso position of that phenylsilane, thereby preventing otherwise competing defunctionalization and isomerization at the stage of the Wheland intermediate. The additive was also found to be crucial for turnover in the alkylation with primary alkyl bromides and for the suppression of transbenzylation in the benzylation with more reactive benzyl bromides. The experimental part of the paper was very detailed, including the reaction process of 1-(Bromomethyl)-4-chlorobenzene(cas: 622-95-7Recommanded Product: 622-95-7)
1-(Bromomethyl)-4-chlorobenzene(cas: 622-95-7) undergoes carbonylation in the presence of dimer of chloro(1,5-cyclooctadiene)rhodium(I) to yield the corresponding phenylacetic acid.Recommanded Product: 622-95-7 It can be synthesized by reacting 4-chlorobenzyl alcohol with bromodimethylsulfonium bromide (BDMS) It can also be synthesized by refluxing a mixture of 4-chlorobenzaldehyde, chlorotrimethylsilane, 1,1,3,3-tetramethyldisiloxane and lithium bromide.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics