84056-07-5

Upstream product

• 98-80-6 phenylboronic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 140-11-4 Benzyl acetate 
• 100-51-6 benzyl alcohol 
• 56139-07-2 (2,3-dimethoxyphenyl)(phenyl)methanol 

Downstream Products

• 94460-88-5 DL-β-<3,4-Dihydroxy-2-benzyl-phenyl>-α-alanin 
• 95820-19-2 2-Acetamino-2-<2-benzyl-veratryl>-malonsaeure-diethylester 
• 93435-27-9 2-Benzyl-veratrumsaeure 

Relevant academic research and scientific papers

Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1 H-Benzotriazoles with Arylboronic Acids

1-(Aryl)methoxy-1H-benzotriazoles (ArCH2OBt) are bench-stable reagents that are prepared readily from 1H-benzotriazol-1-yl-4-methylbenzenesulfonate and benzylic alcohols. These compounds, which contain a N-O-C bond, undergo cross-coupling with arylboronic acids by C-O bond scission with catalysts that comprise Pd(OAc)2 and biarylphosphine ligands. Such reactivity of ArCH2OBt derivatives, which lead to diarylmethanes, has not been described previously and constitutes a new activation of benzylic alcohols. With regard to the various ligand-metal complexes that support catalytic activity, it appears that those with smaller "percent buried volumes" (%Vbur) provide better outcomes. This factor has been evaluated in the initial optimization studies and in further reactions with difficult coupling partners. Ligand electronics of the biaryl moiety seem to play a lesser role in this type of reaction. The biscoordinating bis[(2-diphenylphosphino)phenyl] ether appears to be suitable to improve the yields of low-yielding reactions. Phosphine fine: 1-(Aryl)methoxy-1H-benzotriazoles (ArCH2OBt), which contain a N-O-C bond, undergo cross-coupling with arylboronic acids by C-O bond scission with catalysts that comprise Pd(OAc)2 and biarylphosphine ligands. Such reactivity of ArCH2OBt derivatives, which lead to diarylmethanes, has not been described previously and constitutes a new activation of benzylic alcohols.

Direct alkylation of aromatics using alcohols in the presence of NaHSO 4/SiO2

Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss.

Br?nsted acid-catalyzed synthesis of diarylmethanes under non-genotoxic conditions

Triflic acid and triflimide were found to efficiently catalyze the formation of a wide diversity of diarylmethanes from the non-genotoxic benzylic acetates and electron-rich arenes or heteroarenes. The reaction worked best with acetates capable of generating a stabilized benzylic cationic species. In most cases, the reactions were conveniently run in the absence of solvent under mild conditions.

Tin exchanged heteropoly tungstate: An efficient catalyst for benzylation of arenes with benzyl alcohol

The partial exchange of tin with the protons of 12-tungstophosphoric acid (TPA) results in a highly active heterogeneous catalyst for benzylation of arenes with benzyl alcohol as benzylating agent. The catalysts were characterized by X-ray diffraction, Laser-Raman and FT-IR of pyridine adsorption. The catalytic activity depends significantly on the extent of tin exchanged with the protons of heteropoly tungstate. The characterization results suggest the presence of Lewis acidic sites by the exchange of tin. The catalyst with partial exchange of Sn showed high benzylation activity, which in turn related to variation in acidity of the catalysts. The catalyst is highly active for benzylation reaction irrespective of the nature of substituted arenes and benzyl alcohols. These catalysts are highly active compared to other acid catalysts used for benzylation of different arenes. The catalyst is easy to separate from reaction mixture and exhibit consistent activity upon reuse. The plausible reaction mechanism based on the role of both Lewis and Bronsted acid sites of the catalyst was discussed.

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.