18930-20-6

Upstream product

• 109-99-9 tetrahydrofuran 
• 110-82-7 cyclohexane 
• 108-85-0 1-bromocyclohexane 
• 4441-58-1 4-Cyclohexylidenebutan-1-ol 
• 1940-19-8 1-vinylcyclohexanol 
• 110-83-8 cyclohexene 
• 18930-19-3 1-cyclohexylbutane-1,4-diol 

Relevant academic research and scientific papers

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.

The Combination of Benzaldehyde and Nickel-Catalyzed Photoredox C(sp3)?H Alkylation/Arylation

Herein we report a highly selective photoredox C(sp3)?H alkylation/arylation of ethers through the combination of a photo-organocatalyst (benzaldehyde) and a transition-metal catalyst (nickel). This method provides a simple and general strategy for the C(sp3)?H alkylation/arylation of ethers. A selective late-stage modification of (?)-ambroxide has also been conducted to demonstrate the applicability of the method.

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.

Gold-catalysed cyclic ether formation from diols

Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an SN1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de.