3395-69-5

Upstream product

• 14642-79-6 benzyloxy-trimethylsilane 
• 555-16-8 4-nitrobenzaldehdye 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 100-14-1 4-nitrobenzyl chloride 
• 619-73-8 4-nitrobenzyl chloride 
• 100-39-0 benzyl bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 54184-69-9 2,3-diphenyl-2H-indazole 
• 555-16-8 4-nitrobenzaldehdye 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Reductive Etherification of Aldehydes and Ketones with Alcohols and Triethylsilane Catalysed by Yb(OTf)3: an Efficient One-Pot Benzylation of Alcohols

The one-pot synthesis of symmetrical and unsymmetrical ethers from aldehydes and ketones can be conveniently performed using Yb(OTf)3 as catalyst and triethylsilane as reducing agent in presence of alcohols. This methodology leads to the synthesis of ether derivatives with good yields. Notably, this process resulted a useful tool to protect alcohols as benzyl ether derivatives using differently substituted benzaldehydes as protecting agents under mild conditions. A plausible mechanism was also proposed. (Figure presented.).

Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles

Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.

One-pot etherification of ketones and aldehydes with organic halides using sodium hydride as a reductant

One-pot etherification reaction of aromatic and some aliphatic carbonyl compounds with organic halides in the presence of sodium hydride as a reducing reagent proceeded smoothly in dioxane, a polar solvent with higher boiling point, to provide desired ethers in moderate to high yields. Copyright Taylor & Francis Group, LLC.

Cesium fluoride-Celite: A solid base for efficient syntheses of aromatic esters and ethers

Coupling reactions of a number of aromatic and heteroaromatic phenols with alkyl, acyl or benzoyl halides in acetonitrile with cesium fluoride-Celite are described, demonstrating that this reagent provides an efficient, convenient and practical method for the syntheses of aromatic esters and ethers.

Radical substitution with azide: TMSN3-PhI(OAc)2 as a substitute of in3

TMSN3 and PhI(OAc)2 were found to promote high-yield azide substitution of ethers, aldehydes and benzal acetals. The reaction is fast and occurs at zero to ambient temperature in acetonitrile. However, it is essential for the reaction that TMSN3 is added subsequent to the mixture of PhI(OAc)2 and the substrate. A primary deuterium kinetic isotope effect was found for the azidonation of benzyl ethers both with TMSN3-PhI(OAc)2 and with IN3. Also a Hammett free energy relationship study of this reaction showed good correlation with σ+ constants giving with ρ-values of -0.47 for TMSN 3-PhI(OAc)2 and -0.39 for IN3. On this basis a radical mechanism of the reaction was proposed. The Rayal Society of Chemistry 2005.

A highly efficient method for the reductive etherification of carbonyl compounds with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride

Facile reductive etherification of carbonyl compounds can be conveniently performed by reaction with triethylsilane and alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained in good to excellent yields under mild reaction conditions.

An efficient approach towards syntheses of ethers and esters using CsF-Celite as a solid base

The coupling reactions of a number of alcohols and phenols with alkyl, acyl or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. It has been found that CsF-Celite combinations provide an efficient, convenient and practical method for syntheses of both, ethers and esters.