64655-62-5

Upstream product

• 578-57-4 2-bromoanisole 
• 591-51-5 phenyllithium 
• 529-28-2 4-iodoanisol 
• 119-61-9 benzophenone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 464-72-2 tetraphenylethane-1,2-diol 
• 100-66-3 methoxybenzene 
• 118-55-8 phenyl Salicylate 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 579-75-9 2-Methoxybenzoic acid 
• 4481-56-5 α,α-diphenyl-2-furanmethanol 
• 79654-37-8 diphenyl(2-thienyl)methanol 
• 76-84-6 triphenylmethyl alcohol 
• 16750-63-3 2-methoxyphenylmagnesium bromide 

Downstream Products

• 13561-41-6 N--benzolsulfonamid 
• 119-61-9 benzophenone 
• 92-52-4 biphenyl 
• 2553-04-0 ortho-methoxybenzophenone 
• 86-26-0 2-methoxy-1,1'-biphenyl 
• 6326-60-9 diphenyl(2-hydroxyphenyl)methanol 
• 860586-17-0 1,2-bis-(2-methoxy-phenyl)-1,1,2,2-tetraphenyl-ethane 
• 857591-20-9 2-benzhydryl-4-bromo-anisole 
• 64655-66-9 Diphenyl-(2-methoxy-phenyl)-methyl 
• 94622-89-6 5-bromo-2-methoxy-α,α-diphenylbenzenemethanol 
• 72824-75-0 ((2-methoxyphenyl)methylene)dibenzene 
• 857601-28-6 o-monomethoxytrityl chloride 
• 5062-28-2 2-trityl-anisole 
• 4970-23-4 2-(diphenylmethyl)phenol 

Relevant academic research and scientific papers

Sodium-Ketyl Radical Anions by Reverse Pinacol Reaction and Their Coupling with Iodoarenes

Transition-metal-free C-C bond formation between aryl iodides and pinacols is presented. Pinacols are readily transformed by deprotonation with NaH to their Na-pinacolates. C-C-bond homolysis at room temperature generates in situ the corresponding Na-ketyl radical anions which react with various aryl iodides in a homolytic aromatic substitution reaction to form tertiary Na-alcoholates. Protonation eventually provides tertiary alcohols in an unprecedented route.

Deprotonative metalation of substituted aromatics using mixed lithium-cobalt combinations

The deprotonation of anisole was attempted using different homo- and heteroleptic TMP/Bu mixed lithium-cobalt combinations. Using iodine to intercept the metalated anisole, an optimization of the reaction conditions showed that in THF at room temperature 2 equiv of base were required to suppress the formation of the corresponding 2,2′-dimer. The origin of the dimer was not identified, but its formation was favored with allyl bromide as electrophile. The metalated anisole was efficiently trapped using iodine, anisaldehyde, and chlorodiphenylphosphine, and moderately employing benzophenone, and benzoyl chloride. 1,2-, 1,3-, and 1,4-dimethoxybenzene were similarly converted regioselectively to the corresponding iodides. It was observed that 2-methoxy- and 2,6-dimethoxypyridine were more prone to dimerization than the corresponding benzenes when treated similarly. Involving ethyl benzoate in the metalation-iodination sequence showed that the method was not suitable to functionalize substrates bearing reactive functions.

Palladium-catalyzed arylation of α,α-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls

The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp2-sp3 C-C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.

Convenient Synthesis of Biphenyl-2-carboxylic Acids via the Nucleophilic Aromatic Substitution Reaction of 2-Methoxybenzoates by Aryl Grignard Reagents

Nucleophilic aromatic substitution (SNAr) of 2-methoxybenzoic esters derived from 2,6-dialkylphenols by aryl Grignard reagents affords 1,1'-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2,6-dialkyl-substituents. The phenoxyl protecting groups can be easily removed from the resulting biphenyl-2-carboxylates to the free acids by treatment with potassium hydroxide in aqueous ethanol (2,4,6-trimethylphenyl and 2,6-diisopropylphenyl esters) or sodium methoxide in toluene-hexamethylphosphoric triamide (2,6-di-t-butyl-4-methylphenyl esters). The regioselective biphenyl coupling reaction via the SNAr process is utilized for the key-step construction of the biphenyl skeleton in a formal synthesis of cannabinol.

A Practical and Efficient Method for the Construction of the Biphenyl Framework; Nucleophilic Aromatic Substitution on 2-Methoxybenzoates with Aryl Grignard Reagents

Treatment of 2-methoxybenzoic esters derived from 2,6-dialkylphenols with aryl Grignard reagents afforded 1,1'-biphenyl-2-carboxylates in excellent yields.