40324-40-1

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 108-95-2 phenol 
• 109-99-9 tetrahydrofuran 
• 122-79-2 Phenyl acetate 
• 1927-71-5 4-phenoxybutan-1-ol 
• 1200-03-9 4-bromophenyl butyl ether 
• 351422-19-0 C₁₃H₁₉NO₂S₂ 

Downstream Products

• 108-95-2 phenol 
• 4203-50-3 2-phenoxytetrahydropyran 

Relevant academic research and scientific papers

Copper catalyzed C–O bond formation by direct C–H activation of THF with phenols: an approach to the synthesis of phenyl tetrahydrofuranyl ethers

A direct oxidative transformation of phenol derivatives to the corresponding tetrahydrofuranyl ethers via C–H bond activation, in the presence of copper catalyst and desired products were achieved in good yields using TBHP as an oxidant.

Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

Copper Catalyzed sp3 C-H Etherification with Acyl Protected Phenols

A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato copper(II) phenolates [CuII]-OAr play a key role in this C-O bond forming reaction, formed via transesterification of AcOAr with [CuII]-OtBu intermediates generated upon reaction of [CuI] with tBuOOtBu.

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.

An economic and practical synthesis of the 2-tetrahydrofuranyl ether protective group

Primary, secondary, and tertiary alcohols as well as phenols and carbohydrates are efficiently transformed into the corresponding 2-tetrahydrofuranyl ethers by a combination of Mn(0) powder and CCl4 in tetrahydrofuran.

Efficient and convenient procedure for protection of hydroxyl groups to the THP, THF and TMS ethers and oxidation of these ethers to their aldehydes or ketones in [BPy]FeCl4 as a low cost room temperature ionic liquid

Alcohols were converted to the corresponding THP, THF or TMS ethers in high to excellent yields in 1-n-butylpyridinium chloroferrate media as a stable and low cost room temperature ionic liquid. In addition, oxidation of these ethers to their aldehydes or ketones without any overoxidation reactions in this ionic liquid was also performed.

Tetrahydrofuranylation of alcohols catalyzed by alkylperoxy- λ3-iodane and carbon tetrachloride

Reaction of primary and secondary alcohols with tetrahydrofuran and a catalytic amount of 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one in the presence of carbon tetrachloride at 50°C provides an efficient method for protecting the hydroxy group as 2-tetrahydrofuranyl ethers.

Tetrahydrofuranylation of alcohols using hypervalent iodine reagents

Alcohols are converted to their corresponding 2-tetrahydrofuranyl ethers using (diacetoxyiodo)benzene in THF. Reactions are carried out under reflux, or, more effectively, under microwave irradiation. Yields up to 81% are reported without the use of chlorinated solvents.

A new convenient method for the generation of alkoxy radicals from N-alkoxydithiocarbamates

N-Alkoxydithiocarbamates 2, which can be conveniently prepared from alkyl halides or alcohols using N-methylhydroxydithiocarbamate 1, are very useful precursors of alkoxy radicais.

Acetonyltriphenylphosphonium bromide and its polymer-supported analogues as catalysts in protection and deprotection of alcohols as alkyl vinyl ethers

Both acetonyltriphenylphosphonium bromide (ATPB, 1) and poly-p-styryldiphenylacetonylphosphonium bromide (A) were effective catalysts in the protection of alcohols as THP, THF, and EE ethers as well as the cleavage of THP, THF, and EE ethers to the corresponding alcohols. They could be applied to 1°, 2° and 3° alcohols, phenol and acid-labile alcohols. Both ATPB and catalyst A are excellent catalysts in the present study. It needed only 1×10-2-1.25×10-2 mol equiv. of the polymer-supported catalyst A in the reactions.