Access to α,α-difluoro(arylthio)methyl oxetanes from α,α-difluoro(arylthio)methyl ketones and trimethylsulfoxonium halides: scope, mechanism and applications

Abstract

A general and practical method for the synthesis of α,α-difluoro(arylthio)methyl oxetanes is reported that occurs by the reaction of α,α-difluoro(arylthio)methyl ketones with trimethylsulfoxonium halides. This reaction undergoes the sequential Corey-Chaykovsky...

The [4+1] cyclization reaction of 2-hydroxylimides and trimethylsulfoxonium iodide for the synthesis of 3-amino-2,3-dihydrobenzofurans

“…On the basis of the above results and the literature reports, 9–14 a plausible mechanism of this cyclization reaction of the 2-hydroxylimide and the trimethylsulfoxonium iodide leading to 3-amino-2,3-dihydrobenzofurans was proposed (Scheme 3). The 2-hydroxylimide 1a reacted with NaH to afford the anion 2-hydroxylimide A .…”

Ketyl Radical Enabled Synthesis of Oxetanes

“…27,28 Another approach is the ring expansion of epoxides using sulfur ylides (8). 14,[29][30][31][32][33] However, these methods are predominantly intramolecular transformations and require the stepwise buildup of starting material. Arguably, the Paternò-Büchi (PB) reaction (10), a photochemically promoted [2+2]-cycloaddition between a carbonyl and alkene, is a more direct and straightforward strategy to access oxetanes.…”

Photoredox/copper-catalyzed gem-difluoroalkylation-cyanation of 1,3-enynes

“…The selective incorporation of gem -difluoroalkyl groups into drug-like molecules will have a wide impact on the physicochemical properties and biological activity of the parent molecules, so the development of efficient methods for the incorporation of gem -difluoroalkyl moieties into organic molecules has important value for medicinal chemistry and drug development. 1 In the past decades, visible-light photoredox catalysis has been widely used in the preparation of fluorinated compounds. 2 In 2016, Qing's group disclosed that fluorinated phosphonium salts 2a could serve as the fluoroalkyl radical precursors 3 (Scheme 1a).…”