Synthesis of 2-(trifluoromethylthio)-indenones by silver-mediated cascade trifluoromethylthiolation/cyclization of arylpropynones

Synthesis of Alpha‐trifluoromethylthio Carbonyl Compounds: A Survey of the Methods for the Direct Introduction of the SCF3 Group on to Organic Molecules

“…[18] The products were obtained in moderate to excellenty ields, both with electron-withdrawing and electron-donating groups on the aryl ring. An AgSCF 3 -mediated cascade trifluoromethylthiolation and cyclization process involving alkynesw as also reported by Chen and Zang;a rylpropynonesw ere converted into 2-(trifluoromethylthio)-indenones in the presence of K 2 S 2 O 8 and NaHCO 3 (Scheme 8).…”

“…ChemCatChem 2018ChemCatChem , 10,2717ChemCatChem -2733 www.chemcatchem.org An AgSCF 3 -mediated cascade trifluoromethylthiolation and cyclization process involving alkynesw as also reported by Chen and Zang;a rylpropynonesw ere converted into 2-(trifluoromethylthio)-indenones in the presence of K 2 S 2 O 8 and NaHCO 3 (Scheme 8). [18] The products were obtained in moderate to excellenty ields, both with electron-withdrawing and electron-donating groups on the aryl ring. Moreover,h igh yields werea lso observed when electron rich substitutions are present on the aryl alkyne moiety.…”

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

“…Afterward, Nevado [24], Hopkinson and Glorius [25], Dagousset and Magnier [26], as well as Fu [27] applied this strategy in the synthesis of a series of CH 2 SCF 3substituted heterocycles. For the construction of SCF 3 -substituted cyclic compounds, normally proper alkynes are chosen as the substrates for cascade reactions [28][29][30][31][32]. In 2015, Wang developed an oxidative radical cyclization of aryl alkynoate esters with AgSCF 3 for the synthesis of trifluoromethylthiolated coumarins (Scheme 1b) [28].…”

“…In 2016, Liu exploited the tandem trifluoromethylthiolation/cyclization of N-arylpropiolamides to construct the SCF 3 -substituted spiro [4,5]trienones (Scheme 1c) [29]. In the same year, Zhang and Chen disclosed the transformation of arylpropynones to SCF 3 -substituted indenones through the tandem trifluoromethylthiolation/cyclization processes (Scheme 1d) [30]. As part of our continuing research interest in radical trifluoromethylthiolation reactions [33][34][35][36][37][38], herein we disclose a cascade trifluoromethylthiolation and cyclization of N-[ (3-aryl)propioloyl]indoles to access SCF 3substituted pyrrolo[1,2-a]indol-3-ones (Scheme 1e).…”

Oppenauer-type synthesis of α, β-acetylenic ketones from tetra(phenylethynyl)tin and aromatic aldehydes

“…α-Acetylenic ketones are highly reactive compounds widely used for the synthesis of various carbo-and heterocycles such as pyrroles [1], chromones [2,3], indenones [4], quinolones [5], benzodiazepines [6], spirocycles [7], etc. One of the most general methods for the synthesis of α-acetylenic ketones is based on the reaction of metal acetylides with aldehydes, followed by oxidation of propargyl alcohols formed [2,5,[8][9][10][11].…”