1927-58-8

Upstream product

• 25714-71-0 4-hydroxybutyraldehyde 
• 100-51-6 benzyl alcohol 
• 1191-99-7 2,3-dihydro-2H-furan 
• 109-99-9 tetrahydrofuran 
• 5664-17-5 cyclohexylallene 
• 201230-82-2 carbon monoxide 
• 107-05-1 3-chloroprop-1-ene 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 

Downstream Products

• 4541-14-4 4-benzyloxy-butan-1-ol 
• 2159-32-2 4-(benzyloxy)pentan-1-ol 
• 100-51-6 benzyl alcohol 
• 1383673-18-4 2-benzyloxy-4-hydroxytetrahydrofuran 

Relevant academic research and scientific papers

A convenient synthesis of 2-tetrahydrofuranyl ethers.

[reaction: see text] A wide spectrum of alcohols and phenols are readily transformed to the corresponding 2-tetrahydrofuranyl ethers in good to excellent yields using CrCl2 and CCl4 in THF under nearly neutral conditions at room temperature.

Visible Light-Induced α-C(sp3)-H Acetalization of Saturated Heterocycles Catalyzed by a Dimeric Gold Complex

Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)-H dehydrogenative cross-couplings of ethers, tetrahydrothiophenes, and pyrrolidines were achieved under visible light irradiation by using iodobenzene and an in situ-formed gold complex. The broad functional group compatibility and substrate scope indicate that our strategy is a promising way to synthesize acetal analogues. The method was successfully applied in late-stage modifications of bioactive molecules. Gram scale syntheses and mechanistic studies are also presented.

Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization

C(sp3)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks, and the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp3-rich materials. Herein, we report the stereoselective functionalization of C(sp3)-H bonds of cyclic ethers employing a photochemically active diaryliodonium salt in combination with an anionic phase-transfer catalyst. The synthetic strategy outlined herein allows for regio- and stereochemical control in the α-C-H acetalization of furans and pyrans using alcohol nucleophiles, thus providing the ability to control the configuration at the stereogenic exocyclic acetal carbon.

Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: Reactivity and mechanistic studies

Cross dehydrogenative couplings on ethers occur very effectively using N-fluorobis(phenyl)sulfonimide (NFSI) as oxidizing agent under UVA irradiation in the presence of 2 mol% benzophenone. The reaction was shown to proceed first by fast radical fluorination of the α-C-H bond of ethers, followed by HF elimination to yield the highly electrophilic oxocarbenium ion as a key intermediate.

Unexpected Mild Protection of Alcohols as 2-O-THF and 2-O-THP Ethers Catalysed by Cp2TiCl Reveal an Intriguing Role of the Solvent in the Single-Electron Transfer Reaction

A method for the conversion of primary, secondary and tertiary alcohols into the corresponding THF ethers at room temperature and primary and secondary alcohols into the corresponding THP ethers, has been developed using titanium(III) species generated from a catalytic amount of titanocene dichloride or (4R,5R)-(-)-2,2-dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanolatotitanium(IV) dichloride:acetonitrile adduct together with manganese(0) as a reductant and bromoform in THF or THP as the solvent. A radical mechanism is proposed for this transformation revealing an intriguing role of the solvent in the single-electron transfer reactions catalysed by the low valent TiIII system. A set of primary, secondary and benzylic alcohols have been converted into the corresponding THF and THP ethers and tertiary alcohols into the corresponding THF ethers using a catalytic amount of titanium dichloride in good yields and mild reaction conditions.

CuBr2-promoted tetrahydrofuranylation of alcohols and 1,3-dione

A method for the CuBr2-promoted tetrahydrofuranylation of alcohols and 1,3-dione has been developed. A variety of different alcohols were efficiently converted into the corresponding 2-tetrahydrofuran ethers in the presence of CuBr2. It is noteworthy that this protocol also successfully converted 1,3-diphenyl-1,3-dione into the corresponding 2-tetrahydrofuran derivative in good yield. Georg Thieme Verlag Stuttgart - New York.

Environmentally friendly tetrahydrofuranylation of alcohols using NaHSO4SiO2 under solvent-free conditions

A simple, environmentally friendly, and efficient tetrahydrofuranylation of alcohols has been developed using NaHSO4SiO2 (0.5 mol%) as a catalyst under solvent-free conditions to yield corresponding THF ethers in good to excellent yi

Anhydrous FePO4 as a cost-effective and recyclable catalyst for tetrahydropyranylation and tetrahydrofuranylation of alcohols and phenols

In this article, a mild and efficient protocol for the tetrahydropyranylation and tetrahydrofuranylation of various aliphatic and benzylic alcohols and phenols into their corresponding THP and THF ethers (with 3,4-dihydro- 2H-pyran, DHP and 2,3-dihydrofuran, DHF) has been developed using a catalytic amount of anhydrous FePO4 at room temperature and relatively short reaction times in good to excellent yields.

An economic and efficient tetrahydrofuranylation of alcohols, imines and alkynes

The tetrahydrofuranyl radical, generated by heating tetrahydrofuran in the presence of air and allyl or benzyl chloride, becomes a useful tool in order to transform the hydroxyl functions into ethers, or the CN double bond into amine, or the C-C triple bond into vinyl derivatives. A radical mechanism is proposed followed by a nucleophilic substitution for the alcohol substrate and a radical addition for the iminic and the acetylenic reactants.

New platinum-catalysed dihydroalkoxylation of allenes

A new platinum-catalysed dihydroalkoxylation of alienes is described to give aliphatic acetals by an unexpected attack of two molecules of methanol to the terminal carbon of the aliene moiety. Deuteration experiments suggest an unprecedented formal 1,3-dipolar addition of methanol to a zwitterionic platinum carbene as the key step. The first platinum-catalysed intermolecular carbonbased nucleophile addition to alienes is also reported.