20389-18-8

Upstream product

• 1016-09-7 benzhydryl methyl ether 
• 7647-54-3 N,N-dimethyl-2,2-diphenyl-ethyl-1-amine 
• 100-52-7 benzaldehyde 
• 71-43-2 benzene 
• 185246-56-4 2-phenyl-4,4,6,6-tetradeuterio-5-ethyl-1,3-dioxane 
• 101-81-5 Diphenylmethane 
• 954-67-6 benzhydryl acetate 
• 117-34-0 2,2-diphenylacetic acid 
• 91-01-0 1,1-Diphenylmethanol 
• 778-23-4 deuteriochlorodiphenylmethane 

Downstream Products

• 853-83-8 N-tosyldiphenylmethylamine 
• 954-67-6 benzhydryl acetate 
• 109495-69-4 acetic acid-(α-deuterio-benzhydryl ester) 

Relevant academic research and scientific papers

Scandium(III) Triflate-Catalyzed Friedel-Crafts Alkylation Reactions

The Sc(OTf)3-catalyzed Friedel-Crafts alkylation reaction with an alcohol, an arenecarbaldehyde or an arenecarbaldehyde acetal as the alkylating agent affords a diarylmethane or an allylbenzene derivative highly selectively. The salient feature of this reaction is that only a catalytic amount of Sc(OTf)3 can effect the reaction. Furthermore, Sc(OTf)3 is recoverable and reusable after the synthetic reaction. The Sc(OTf)3-catalyzed benzylation using an arenecarbaldehyde and 1,3-propanediol or their acetal affords diarylmethane as a sole product in excellent yields in sharp contrast to the original Friedel-Crafts reaction. Since no reaction occurs in the absence of 1,3-propanediol, the reaction is considered to proceed through a redox process including a hydride shift. The hydride shift mechanism is strongly supported by the experimental evidence. The reaction of benzaldehyde with benzene in the presence of 1,3-propanediol-1,1,3,3,-d4 gives rise to the deuterium incorporation into the benzylic carbon of diphenylmethane. Worthy of note is that 1,3-propanediol acts as the hydride source. Herein, diphenylmethyl 3-hydroxypropyl ether is assumed to be the most likely intermediate. In this reaction, Sc(OTf)3 catalyst effectively promotes initial acetal formation, electrophilic aromatic substitution, and successive intramolecular hydride transfer.

Room-Temperature Palladium-Catalyzed Deuterogenolysis of Carbon Oxygen Bonds towards Deuterated Pharmaceuticals

Site-specific incorporation of deuterium into drug molecules to study and improve their biological properties is crucial for drug discovery and development. Herein, we describe a palladium-catalyzed room-temperature deuterogenolysis of carbon–oxygen bonds

Method for constructing carbon-hydrogen bond by catalyzing alcohol dehydroxylation with palladium/platinum

The invention discloses a method for constructing a carbon-hydrogen (deuterium) bond. The method comprises the following step: in the presence of a palladium/platinum catalyst and aryl halide, an alcohol hydroxyl group of an alcohol and hydrogen (deuterium) gas is replaced by hydrogen (deuterium) to construct the carbon-hydrogen (deuterium) bond. According to the method, the palladium/platinum catalyst is used as a catalyst, the green hydrogen (deuterium) gas is used as a hydrogen (deuterium) source, efficient alcohol dehydroxylation is performed at room temperature to construct the carbon-hydrogen (deuterium) bond, and the method is particularly suitable for constructing the carbon-deuterium bond and can be widely applied to synthesis of deuterated drugs.

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Metal catalyst-free substitution of allylic and propargylic phosphates with diarylmethyl anions

Substitution of secondary allylic phosphates with the anions derived from Ar2CH2 with BuLi or LDA proceeded regioselectively and stereoselectively without a metal catalyst, affording inversion products in good yield. Similarly, propargylic phosphates gave propargylic products selectively.

Facile and convenient method of deuterium gas generation using a Pd/C-catalyzed H2-D2 exchange reaction and itsapplication to synthesis of deuterium-labeled compounds

The Pd/C-catalyzed H2-D2 exchange reaction using a H2-D2O combination provided a general, efficient and environmentally friendly route for the preparation of deuterium gas (D 2). H2 sealed

Superacid-Catalyzed Reductive Friedel-Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals

Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethane-sulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph2CHOCH2CH2CH2OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel-Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol

Scandium(III) trifluoromethanesulfonate catalyses the Friedel-Crafts benzylation of aromatic compounds with arenecarbaldehydes and propane-1,3-diol to produce, through a clean redox process, diarylmethanes in high to excellent yields.

Reductive electrophilic substitution of diarylmethyl methyl ethers: Synthetic applications

The reductive cleavage of diarylmethyl methyl ethers with Li metal in THF led to quantitative formation of the corresponding diarylmethyl anions. Quenching with electrophiles afforded substituted diarylmethanes in good to excellent yields.