3208-32-0

Upstream product

• 99175-06-1 2-(5-chloro-hexyl)-tetrahydro-furan 
• 1191-99-7 2,3-dihydro-2H-furan 
• 89583-95-9 Hexylmagnesiumiodid 
• 693-25-4 n-pentylmagnesium bromide 
• 123136-04-9 Trifluoro-methanesulfonic acid tetrahydro-furan-2-ylmethyl ester 
• 74581-34-3 4-Methylselanyl-decan-1-ol 
• 122976-53-8 4-acetoxy-1-bromdecane 
• 74581-35-4 4-Phenylselanyl-decan-1-ol 
• 124-18-5 decane 
• 79131-68-3 5-hexyltetrahydrofuran-2-ol 
• 207669-70-3 γ-thionodecalactone 
• 112-47-0 1,10-Decanediol 
• 7664-93-9 sulfuric acid 
• 57074-37-0 (Z)-4-decen-1-ol 

Downstream Products

• 57032-39-0 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-C-methyl-α-D-xylo-hex-5-enofuranose 

Relevant academic research and scientific papers

Zeolites efficiently promote the cyclization of nonactivated unsaturated alcohols

Excellent cyclization: Zeolites H-BEA, H-MFI, H-FAU, and H-STF were found to be efficient, selective, and reusable catalysts in the cyclization of cis-4-decenol, affording the corresponding tetrahydrofuran with excellent yields to provide a new synthetic route to alkylfurans. Bronsted and Lewis acid sites in the zeolites under study are probably the active sites, because both of them catalyze this reaction.

An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans

The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst

A Pt-loaded TiO2 photocatalyst successfully catalyzed the direct cross-coupling between various alkenes and tetrahydrofuran (THF) without any additional oxidizing agent. The reaction between cyclohexene and THF gave three cross-coupling products, namely, 2-cyclohexyltetrahydrofuran (A), 2-(cyclohex-2-en-1-yl)tetrahydrofuran (B) and 2-(cyclohex-1-en-1-yl)tetrahydrofuran (C), along with gaseous hydrogen. The mechanistic study revealed that these products were formed through different individual mechanisms: successive addition of two radical species, a 2-tetrahydrofuranyl radical and a hydrogen radical, to the double bond of cyclohexene for A, coupling of a 3-cyclohexenyl radical and a 2-tetrahydrofuranyl radical for B, and 2-tetrahydrofuranyl radical addition and hydrogen radical elimination at the double bond of cyclohexene for C. Among these three mechanisms, those for B and C are dehydrogenative. In this photocatalytic reaction system, since the cyclohexene molecule has enough reactivity, due to the localized π electron density, the Pt nanoparticles loaded on the TiO2 function not as a metal catalyst but as an electron receiver to enhance the charge separation, although the dehydrogenative cross-coupling of benzene with THF requires Pd metal catalysis.

Bifunctional property of Pt nanoparticles deposited on TiO2 for the photocatalytic sp3C-sp3C cross-coupling reactions between THF and alkanes

The photocatalytic sp3C-sp3C cross-coupling between tetrahydrofuran (THF) and various alkanes was accomplished with Pt loaded titanium oxide (Pt/TiO2) photocatalysts. The cross-coupling between THF and cyclohexane was systematically studied, which revealed that the reaction followed two routes: the main course was the photooxidation of both substrates on a Pt/TiO2 photocatalyst to generate radical species followed by their successive coupling; meanwhile, the minor one was a hybrid of photocatalysis by Pt/TiO2 and thermocatalysis by Pt metal nanoparticles. The activity of the Pt catalysis was suggested to consist in the activation of an sp3C-H bond in THF or alkane molecules adsorbed on its surface and promote the reaction between the activated molecules and photogenerated radical species. Thus, the Pt nanoparticles on TiO2 were believed to play a bifunctional role of an electron receiver as well as a metal catalyst.

An efficient method for the reductive conversion of acyclic esters to ethers via a TMS-protected acetal

We report an efficient two step process for the reduction of non-aromatic esters to the corresponding ethers via the intermediate TMS-protected acetal. The acetal formed after the first step can be carried on directly to the subsequent reduction to the ether without purification. The ester reduction step was monitored using in-situ ReactIR for disappearance of the C[dbnd]O peak, allowing for the exact determination of time and equivalents of the reducing agent. Furthermore, use of TMS-imidazole to form the acetal has allowed us to dramatically reduce the overall reaction time required for the two step procedure.

Simple salts of abundant metals (Fe, Bi, and Ti) supported on montmorillonite as efficient and recyclable catalysts for regioselective intramolecular and intermolecular hydroalkoxylation reactions of double bonds and tandem processes

The transfer of catalytic hydroalkoxylation reactions of olefins from homogeneous to heterogeneous conditions has been studied using two types of solid catalysts, namely montmorillonite (MMT) doped with metal cations and metal nanoparticles supported on oxides. In the case of intramolecular reactions, 38-99% yields of cyclic ethers have been obtained using Fe-MMT and Bi-MMT both in CH3NO2 and dimethyl carbonate (DMC) compared with other supported metal salts or metal nanoparticles. In the case of more challenging intermolecular reactions, conversions up to 72% and yields up to 54% were obtained with metal-doped MMT as well, such as Fe-, Bi-, and Ti-MMT. In this paper, we detail the substrate scope and limitations for both classes of reactions and tandem processes, their transposition in flow and some mechanistic insights concerning the active species, in processes identified as truly heterogeneously catalysed. As a general trend, it was observed that trisubstituted double bonds allowed the best results both in intra- and intermolecular reactions. The transfer of homogeneous catalysts onto heterogeneous ones in the case of Fe-MMT and Bi-MMT was successful and even allowed enhanced catalytic activities in the case of Bi-MMT.

Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents

We describe herein an efficient and particularly sustainable catalytic system for the intramolecular hydroalkoxylation of double bonds. A heterogeneous catalyst based on the impregnation of benign metals such as iron and bismuth on montmorillonite was used for a highly atom-economic transformation in DMC, a non-VOC solvent. The transformation allowed the formation of a large range of cyclic ethers from the corresponding unsaturated alcohols and the catalyst could be recycled several times.

Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters

Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity. An assist from Al: A bifunctional catalyst system consisting of a Ru/phosphine complex and aluminum triflate allows selective hydrogenation of esters to ethers. A variety of lactones were reduced to the desired products in good yields. The catalyst further provides a general method for the reduction of linear esters and reductive etherification of carboxylic acids with alcohols.

Nickel complex catalyzed efficient activation of sp3and sp 2c-h bonds for alkylation and arylation of oxygen containing heterocyclic molecules

A nickel(II) complex (1) of N,N'-bis(2,6-diisopropylphenyl)-2,6- pyridinedicarboxamido (L) ligand was examined for catalytic coupling of Grignard reagents with the C-H bond of oxygen containing heterocyclic compounds such as tetrahydrofuran and furan. The nickel( II) complex showed excellent activity in catalyzing C-H activation and further coupling with various Grignard reagents. The effective activation of the C-H bond proceeded under ambient reaction conditions with a short reaction time (1-2 h). The catalyst (1) displays high turnover frequency of 4,130 h-1with catalyst loading as low as 0.01 mol%. This catalytic route could prove to be an efficient mode of activation of sp3and sp2C-H bonds in various heterocycles for the preparation of synthetically and pharmaceutically relevant molecules. Springer Science+Business Media New York 2013.