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Upstream product

• 426-73-3 2,2-bis-(4-fluoro-phenyl)-1,2-diphenyl-ethanone 
• 379-55-5 bis(4-fluorophenyl)phenylmethanol 
• 93-58-3 benzoic acid methyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 
• 345-92-6 4,4'-Difluorobenzophenone 
• 289656-82-2 bis(4-fluorophenyl)phenylacetonitrile 
• 100-58-3 phenylmagnesium bromide 
• 1359298-96-6 C₁₉H₁₃F₂⁽¹⁺⁾*BF₄^(1-) 
• 587-79-1 4-fluorodiphenylmethane 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant academic research and scientific papers

Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes

Palladium-catalyzed cross-coupling reactions have become one of the most useful tools in modern organic chemistry. Current methods to achieve direct functionalization of sp3 C-H bonds of arenes and heteroarenes often employ substrates with appropriately placed directing groups to enable reactivity. Examples of intermolecular arylation methods of weakly acidic sp3 C-H bonds in the absence of directing groups, however, are still limited. We describe herein a study on the use of additives in Pd-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds of diarylmethanes with aryl bromides at room temperature. These studies resulted in development of four new efficient Pd-catalyzed DCCP using additives that enabled the generation of a range of sterically and electronically diverse aryl- and heteroaryl containing triarylmethanes in good to excellent yields. Additive identification and optimization of all reaction conditions (additive loading, solvent and temperature) were performed using high-throughput experimentation (HTE). The approach outlined herein is expected to be generalizable to other C-H functionalization reactions involving the deprotonation of weakly acidic C-H bonds. The Royal Society of Chemistry 2013.

Towards a comprehensive hydride donor ability scale

Rates of hydride transfer from several hydride donors to benzhydrylium ions have been measured at 20 °C and used for the determination of empirical nucleophilicity parameters N and sN according to the linear free energy relationship log k20 °C=sN(N+E). Comparison of the rate constants of hydride abstraction by tritylium ions with those calculated from the reactivity parameters sN, N, and E showed fair agreement. Therefore, it was possible to convert the large number of literature data on hydride abstraction by tritylium ions into N and sN parameters for the corresponding hydride donors, and construct a reactivity scale for hydride donors covering more than 20 orders of magnitude.

Process development and optimization for production of a potassium ion channel blocker, ICA-17043

A scalable process for the manufacture of a potassium ion channel blocker was developed and optimized. Key features of the process include an optimized Grignard reaction, a direct cyanation of the intermediate trityl alcohol derivative, and an improved nitrile hydrolysis protocol, relative to the original acidic hydrolysis conditions, to generate the crude active pharmaceutical ingredient (API) with >95% HPLC purity. The Grignard and the cyanation reactions could be telescoped, resulting in an improved throughput compared to the original four-step process. An effective recrystallization of the API was also developed and the process scaled up to manufacture multiple batches at the pilot scale.

The Reduction of Fluorine-containing Triarylmethanols by Formic Acid

Triarylmethanols containing one or more fluorine substituents in the para-positions are converted by 90 percent formic acid into a mixture of the fluorine-containing triarylmethane, and a second component in which one fluorine has been replaced by a hydro