F–-Free Deoxyhydrotrifluoromethylation of α-Keto Esters with Ph3P+CF2CO2–: Synthesis of α-CF3-Substituted Esters was written by Zheng, Ying;Jia, Yimin;Yuan, Yuan;Jiang, Zhong-Xing;Yang, Zhigang. And the article was included in Journal of Organic Chemistry in 2020.Category: tetrahydrofurans This article mentions the following:
Trifluoromethylated compounds are usually obtained via trifluoromethylation reaction by the use of CF3SiMe3 and NaSO2CF3, Umemoto’s and Togni’s reagents. Here, an external fluorine anion-free direct deoxyhydrotrifluoromethylation of α-keto esters with a difluoromethylating reagent has been achieved, in which the employment of water can promote the dissociation of the CF2 group to form a CF3 moiety, which provides the successful transformation. The current protocol demonstrates one of the most practical approaches to generate α-trifluoromethyl esters with a broad substrate scope and high functional group compatibility, in which it is applicable to late-stage modification of biol. active compounds and can be readily scaled up. Mechanistic investigation reveals that an in situ-generated gem-difluoroalkene intermediate is decomposed by water, giving rise to acid fluoride and HF. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Category: tetrahydrofurans).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Category: tetrahydrofurans
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem