860376-18-7

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 28987-79-3 m-tolylmagnesium bromide 
• 1192263-63-0 C₁₅H₂₃ClO 
• 108-88-3 toluene 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 22184-24-3 o-chlorobenzyl acetate 
• 16419-60-6 2-Methylphenylboronic acid 
• 98-51-1 4-tert-butyltoluene 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 

Downstream Products

• 859791-11-0 2-(3-methylbenzyl)benzonitrile 

Relevant academic research and scientific papers

Synthetic method of diarylmethanes

The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water

A convenient procedure employing simple starting materials benzyl alcohols and acetates as the benzyl donors to assemble a series of diarylalkanes through benzylation of arenes using in situ prepared superacid BF3-H 2O as an efficient promoter has been developed. The beneficial role of water in the reaction has been clarified with combination of control experiments and 11B NMR analysis. This reaction is a self-promoted model, which is triggered by the trace of water and continuously promoted by self released by-product water (or carboxylic acid). A wide range of substrates are investigated and the moderate to excellent yields and the good regioselectivities for secondary benzyl alcohols as well as arenes bearing electron-withdrawing groups have been achieved. As a result, moisture in the reaction system has been utilized as an efficient initiator in all benzylation cases.

Benzylation of arenes with benzyl ethers promoted by the in situ prepared superacid BF3-H2O

An efficient and environmentally friendly benzylation of arenes with benzyl ethers as benzyl donors using BF3-Et2O to generate in situ the superacid BF3-H2O as an efficient promotor has been described. A wide variety of functional groups have been investigated and found to be compatible to give the desired diarylmethanes in yields of up to 99%. The crucial role of the moisture content in this transformation has been demonstrated by detailed investigations. This journal is the Partner Organisations 2014.

ARYLALKYLATION OF 4-tert-BUTYLTOLUENE WITH SUBSTITUTED BENZYL CHLORIDES

The reaction of 4-alkylbenzyl chlorides with 4-tert-butyltoluene in the presence of titanium tetrachloride and ferric chloride leads to the formation of 2-methyl-4'-alkyl-5-tert-butyldiphenylmethanes.The arylalkylation of 4-tert-butyltoluene with 2- and 4-chlorobenzyl chlorides, catalyzed by titanium tetrachloride, leads to the formation of mixtures of 2-methyl-5-tert-butyldiphenylmethane, 2-tert-butyl-5-methyldiphenylmethane, and isomeric methyldiphenylmethanes containing a chloride atom in the benzyl fragment.The products of the reaction catalyzed by ferric chloride do not contain 2-tert-butyl-5-methylchlorodiphenylmethanes.The reacti on of 4-nitrobenzyl chloride with 4-tert-butyltoluene in the presence of ferric chloride leads to the formation of a mixture of 2-methyl-4'-nitro-5-tert-butyldiphenylmethane and isomeric methylnitrodiphenylmethanes.Under the influence of AlCl3-CH3NO2 in benzene 2,4'-dimethyl-5-tert-butyldiphenylmethane eliminates both the 4-methylbenzyl group and the tert-butyl group.Under analogous conditions 2-methyl-5-tert-butyldiphenylmethanes containing a chlorine atom or a nitro group in the benzyl fragment are dealkylated with the elimination of only the tert-butyl group.