35896-48-1Relevant articles and documents
Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light
Liu, Peng,Liu, Wenbo,Li, Chao-Jun
supporting information, p. 14315 - 14321 (2017/10/17)
The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane
Kong, Han Il,Crichton, Jennifer E.,Manthorpe, Jeffrey M.
supporting information; experimental part, p. 3714 - 3717 (2011/08/06)
α-Trifluoromethanesulfonyl esters, ketones and amides are C-H acids capable of reacting with trimethylsilyldiazomethane to afford the corresponding ambiphilic alkenes. While esters were found to be non-selective, ketones were highly regioselective for O-methylation and displayed variable E/Z stereoselectivity. Amides were observed to be both highly regio- and stereoselective, affording O-methylation with exclusive formation of the Z-alkene.
Stereospecific alkenylation of C-H bonds via reaction with β- heteroatom-functionalized trisubstituted vinyl triflones
Xiang, Jason,Jiang, Wanlong,Gong, Jianchun,Fuchs
, p. 4123 - 4129 (2007/10/03)
Aryl and alkyl β-heteroatom-trisubstituted vinyl triflones react with THF and cyclohexane to undergo trifluoromethyl radical-mediated C-H functionalization reactions to afford E and Z β-heteroatom-trisubstituted olefins. Most reactions proceed with both high yield and high stereospecificity (retention of configuration). β-Substituents which have been employed in this study are iodine, bromine, fluorine, benzoate, ethylcarbonate, and phthalimide. β-Substituents bearing powerful electron- releasing groups such as alkoxy or amino render the vinyl triflone unreactive.
