1155878-26-4Relevant articles and documents
The Electrophilic Fluorination of Enol Esters Using SelectFluor: A Polar Two-Electron Process
Wood, Susanna H.,Etridge, Stephen,Kennedy, Alan R.,Percy, Jonathan M.,Nelson, David J.
supporting information, p. 5574 - 5585 (2019/03/21)
The reaction of enol esters with SelectFluor is facile and leads to the corresponding α-fluoroketones under mild conditions and, as a result, this route is commonly employed for the synthesis of medicinally important compounds such as fluorinated steroids. However, despite the use of this methodology in synthesis, the mechanism of this reaction and the influence of structure on reactivity are unclear. A rigorous mechanistic study of the fluorination of these substrates is presented, informed primarily by detailed and robust kinetic experiments. The results of this study implicate a polar two-electron process via an oxygen-stabilised carbenium species, rather than a single-electron process involving radical intermediates. The structure–reactivity relationships revealed here will assist synthetic chemists in deploying this type of methodology in the syntheses of α-fluoroketones.
Palladium-catalyzed direct α-arylation of α-fluoroketones: A straightforward route to α-fluoro-α-arylketones
Guo, Chen,Wang, Ruo-Wen,Guo, Yong,Qing, Feng-Ling
experimental part, p. 86 - 96 (2012/02/05)
The palladium-catalyzed direct α-arylation of both open-chain and cyclic α-fluoroketones by using P(o-tolyl)3 or RuPhos as ligand and K3PO4·3H2O as mild base has been developed. This method allows a variety of q
Pd-catalyzed arylation of silyl enol ethers of substituted α-fluoroketones
Guo, Yong,Twamley, Brendan,Shreeve, Jean'Ne M.
experimental part, p. 1716 - 1722 (2009/06/28)
α-Fluoro-α-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either α-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an α-fluoroketone requires a strong base, such as potassium tert-b
