1359975-45-3Relevant academic research and scientific papers
Cobalt-catalyzed oxidative cyclization of gem-disubstituted conjugated alkenols
Alves, Tania M.F.,Costa, Mateus O.,Bispo, Beatriz A.D.,Pedrosa, Fabiana L.,Ferreira, Marco A.B.
, p. 3334 - 3338 (2016/07/11)
Aryl gem-disubstituted conjugated alkenols underwent oxidative cyclization affording 2,5,5-trisubstituted tetrahydrofurans in reasonable yields and good diastereoselectivities using the reductive termination variation of the Mukaiyama aerobic oxidative reaction. Under oxidative termination, the same alkenols produced diols and ketonic by-products via the double hydration and beta-scission competing pathways. Furthermore, the differences in alkenol reactivity under the reductive and oxidative termination conditions were investigated.
Water opens the door to organolithiums and Grignard reagents: Exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans
Cicco, Luciana,Sblendorio, Stefania,Mansueto, Rosmara,Perna, Filippo M.,Salomone, Antonio,Florio, Saverio,Capriati, Vito
, p. 1192 - 1199 (2016/02/09)
It has always been a firm conviction of the scientific community that the employment of both anhydrous conditions and water-free reaction media is required for the successful handling of organometallic compounds with highly polarised metal-carbon bonds. Herein, we describe how, under heterogeneous conditions, Grignard and organolithium reagents can smoothly undergo nucleophilic additions to γ-chloroketones, on the way to 2,2-disubstituted tetrahydrofurans, "on water", competitively with protonolysis, under batch conditions, at room temperature and under air. The reactivity of the above organometallic reagents has also been investigated in conventional anhydrous organic solvents and in bio-based eutectic and low melting mixtures for comparison. The scope and limitations of this kind of reaction are discussed.
New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction
Singh, Parvinder Pal,Gudup, Satish,Aruri, Hariprasad,Singh, Umed,Ambala, Srinivas,Yadav, Mahipal,Sawant, Sanghapal D.,Vishwakarma, Ram A.
experimental part, p. 1587 - 1597 (2012/03/22)
We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic unbranched and branched aliphatic ethers via activation of C(sp3)-H. In the presence of 1 mol% of iron oxide, five and six membered unbranched cyclic ethers such as tetrahydrofuran and tetrahydropyran gave good to excellent yields of cross-coupled products. Whereas, in case of branched ether such as 2-methyltetrahydrofuran, it was observed that the arylation occurred at both the sides and gave moderate yields of a mixture of regioisomers. Among the organometallic species used, alkyl organometallic reagents gave less yields as compared to aryl organometallics.
