Copper-Catalyzed 6-endo-dig Cyclization-Coupling of 2-Bromoaryl Ketones and Terminal Alkynes toward Naphthyl Aryl Ethers in Water was written by Su, Lebin;Xie, Shimin;Dong, Jianyu;Pan, Neng;Yin, Shuang-Feng;Zhou, Yongbo. And the article was included in Organic Letters in 2022.Application In Synthesis of (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 This article mentions the following:
The cyclization-coupling reaction of 2-bromoaryl ketones 2-Br-4-R-5-R1C6H2C(O)Me (R = H, Cl, F, MeO; R1 = H, Cl, Me), 1-(pyridin-3-yl)ethan-1-one and terminal alkynes R2CCH (R2 = Ph, 4-bromophenyl, pyridin-3-yl, etc.) is first realized by copper catalysis, which produces polyfunctional naphthyl aryl ethers I (X = CH, N) in moderate to excellent yields with broad substrate scope and good functional group tolerance. This reaction proceeds via 6-endo-dig cyclization and C(sp2)-O coupling using green H2O as the unique solvent and 5-bromopyrimidin-2-amine as the critical additive. Mechanistically, a unique Cu(III)-acetylide probably is the key intermediate, which allows exclusive 6-endo-dig selectivity. 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: 582-52-5Application In Synthesis of (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).
(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. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Application In Synthesis of (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
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem