Silver-Catalyzed Nucleophilic Deoxydifluoromethylthiolation of Activated Aliphatic Alcohols with BT-SCF2H was written by Tironi, Matteo;Hopkinson, Matthew N.. And the article was included in European Journal of Organic Chemistry in 2022.Electric Literature of C8H10O2 This article mentions the following:
Deoxygenative conversion of alcs. into difluoromethylthioethers is reported using 2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium triflate (BT-SCF2H) as a source of –SCF2H anions. The presence of silver(I) triflate as a catalyst was found to be crucial for stabilizing the in situ-generated anion, while the concomitant formation of a reactive 2-(alkoxy)benzothiazolium electrophile likely ensures a fast onward substitution reaction, avoiding the build-up of –SCF2H. To the best of authors’ knowledge, this process represents the first report of a direct nucleophilic substitution reaction with –SCF2H and delivers products containing the medicinally relevant difluoromethylthio motif in a single step from widely available alcs. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Electric Literature of C8H10O2).
(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Electric Literature of C8H10O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem