32189-55-2

Upstream product

• 954-16-5 2,4,6-Trimethylbenzophenon 
• 100-52-7 benzaldehyde 
• 2633-66-1 2-mesitylmagnesium bromide 
• 592-41-6 1-hexene 
• 1146-83-4 4-Bromo-2',4',6'-trimethylbenzophenone 
• 487-68-3 mesytaldehyde 
• 6279-93-2 2-Bromophenyl mesityl ketone 
• 1146-81-2 3-Bromophenyl mesityl ketone 
• 64-17-5 ethanol 
• 98-80-6 phenylboronic acid 
• 1711-09-7 3-bromobenzoyl chloride 
• 7154-66-7 2-bromobenzoic acid chloride 
• 108-67-8 1,3,5-trimethyl-benzene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 22521-95-5 2,4,6-trimethyl-benzhydryl chloride 
• 1517-60-8 2,4,6-Trimethyl-benzhydrol 
• 33241-90-6 (+/-)-benzoic acid-(2,4,6-trimethyl-benzhydryl ester) 
• 37834-57-4 bis-(2,4,6-trimethyl-benzhydryl)-ether 
• 4453-79-6 2-benzyl-1,3,5-trimethylbenzene 
• 32189-30-3 (+/-)-Brom-phenyl-(2,4,6-trimethyl-phenyl)-methan 
• 954-16-5 2,4,6-Trimethylbenzophenon 
• 33708-11-1 (+/-)-Methoxy-phenyl-<2,4,6-trimethyl-phenyl>-methan 
• 69639-56-1 p-tolyl-(2,4,6-trimethyl-benzhydryl)-sulfide 
• 807632-47-9 mesityl(phenyl)methyl acetate 
• 911485-07-9 (+/-)-phthalic acid mono-(2,4,6-trimethyl-benzhydryl ester) 

Relevant academic research and scientific papers

Mesityllithium and p-(dimethylamino)phenyllithium for the selective alternate trilithiation of the hexaphenylbenzene framework

We report mesityllithium and p-(dimethylamino)phenyllithium as new valuable lithiating reagents, which realize Br/Li exchange reaction of bromoarenes at relatively high temperature in THF. With these reagents, we established the general and practical protocols for the selective alternate trilithiation of the hexaphenylbenzene framework. This journal is the Partner Organisations 2014.

Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes to Form Hindered Secondary Alcohols

Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).

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.).

AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage

A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.

Visible light photoredox-catalyzed deoxygenation of alcohols

Carbon-oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon-oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)2( dtb-bpy)](PF6 ) as visible light photocatalyst and Hünig's base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C-F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.

Chelating alkoxy NHC-Rh(I) complexes and their applications in the arylation of aldehydes

In this study, new rhodium(I) complexes (5 and 6) have been prepared by the reaction of [RhCl(COD)]2 with a series of imidazolium salts (3 and 4), which were obtained from a chiral amino alcohol. The catalytic activities of these complexes were tested in the arylation of aldehydes. It was found that the synthesized rhodium complexes were highly effective catalysts for the arylation of aldehydes in short reaction times (5 min, TOF = 1193 h -1). However, the obtained ee values (up to 32% ee) remained low. We have proposed a mechanism for the arylation reaction of aldehydes, which is confirmed via 19F NMR spectroscopy.

N-heterocyclic carbene complexes of Rh(I) and electronic effects on catalysts for 1,2-addition of phenylboronic acid to aldehydes

1,3-Diarylsubstituted imidazolinium salts, (NHC-H)Cl, 3, containing hydrogen or alkyl groups at the 4,5-positions of the imidazolidine ring, served as precursors to rhodium(I) complexes [RhCl(NHC)COD], 4, which were converted into cis-[RhCl(NHC)(CO)2] complexes, 5. All compounds prepared were characterized by elemental analyses, 1H NMR and 13C NMR. The relative σ-donor/π-acceptor strength of the NHC ligands was determined by means of IR spectroscopy of 5. The ability of NHCs in 4 to enchance activity was explored in the 1,2-addition of phenylboronic acid to aldehydes. A good correlation was observed between catalytic activity and the electron-donating power of the NHC ligands.

Convenient synthesis of triarylmethanes and 9,10-diarylanthracenes by alkylation of arenes with aromatic aldehydes using acetyl bromide and ZnBr2/SiO2

Reaction of electron-rich arenes with acetyl bromide and aldehydes in the presence of silica gel-supported zinc bromide was carried out in benzene to give selectively the corresponding triarylmethanes or 9,10-diarylanthracenes in high yields depending upon the ratio of an arene and an aldehyde. The mild conditions employed are especially noteworthy.

Synthesis and use of mono- or bisxylyl linked bis(benzimidazolium) bromides as carbene precursors for C-C bond formation reactions

Two benzimidazolium moieties linked by one or two xylyls (m- and p-) have been synthesized, characterized and then they were used for Heck coupling reactions as in situ formed catalysts. Mono bridged salts are more efficient as compared to bisbridged salts. In addition, mono bridged salts were converted to Rh-NHC complexes which were tested as catalysts for the arylation of aldehydes.

In situ preparation of rhodium/N-heterocyclic carbene complexes and use for addition of arylboronic acids to aldehydes

(Chemical Equation Presented) The in situ prepared three component system [RhCl(COD)]2/imidazolidinium salts (2, 4) and KOBut catalyses the addition of phenylboronic acid to sterically hindered aldehydes affording the corresponding arylated secondary alcohols in good yields. Four novel 1,3-dialkylimidazolidinium (2-4) salts as NHC precursors were synthesized from N,N′-dialkylethylenediamine.