73475-34-0

Upstream product

• 119-61-9 benzophenone 
• 395-47-1 [2-(trifluoromethyl)phenyl]magnesium bromide 
• 76-84-6 triphenylmethyl alcohol 
• 79654-37-8 diphenyl(2-thienyl)methanol 
• 4481-56-5 α,α-diphenyl-2-furanmethanol 
• 392-83-6 o-trifluoromethylphenyl bromide 

Downstream Products

• 119-61-9 benzophenone 
• 92-52-4 biphenyl 
• 727-99-1 2-trifluoromethylbenzophenone 
• 362-59-4 2-trifluoromethyl-biphenyl 
• 37594-84-6 1-(2-trifluoromethyl-trityl)-1H-imidazole 
• 73475-39-5 2-(trifluoromethyl)triphenylmethane 
• 73475-38-4 9-(2-trifluoromethylphenyl)fluorene 

Relevant academic research and scientific papers

(2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow

We report the on-demand generation of hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be a very useful reagent and undergoes in-line Br/Na-exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb-amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale-up of the Br/Na-exchange using an in-line electrophile quench was also reported.

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.