27047-19-4

Upstream product

• 108-98-5 thiophenol 
• 99-73-0 para-bromophenacyl bromide 
• 930-69-8 sodium thiophenolate 
• 882-33-7 diphenyldisulfane 
• 29425-81-8 (4-bromophenyl)(3-phenyloxiran-2-yl)methanone 
• 99-90-1 para-bromoacetophenone 
• 96928-03-9 2-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1-(4-chloro-benzyl)-4,6-diphenyl-pyridinium; bromide 
• 96928-05-1 2-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1-(4-methyl-benzyl)-4,6-diphenyl-pyridinium; bromide 
• 96928-01-7 1-Benzyl-2-[2-(4-bromo-phenyl)-2-oxo-ethylsulfanyl]-4,6-diphenyl-pyridinium; bromide 
• 96928-07-3 2-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-1-methyl-4,6-diphenyl-pyridinium; bromide 

Downstream Products

• 102880-95-5 2-bromo-1-(4-bromo-phenyl)-2-phenylsulfanyl-ethanone 
• 1380501-90-5 2-(4-bromophenyl)-4-(3-chloropropyl)furan 
• 1380501-86-9 4-(2-(benzyloxy)ethyl)-2-(4-bromophenyl)furan 
• 1380501-73-4 2-(4-bromophenyl)-4-hexylfuran 
• 56241-26-0 methylphenylsulfonium 4-bromophenacylide 
• 1380501-84-7 2-(4-bromophenyl)-4-cyclohexylfuran 
• 511552-70-8 C₁₆H₁₇BrO 
• 100965-06-8 4-(4-bromo-phenyl)-5-phenylsulfanyl-3H-thiazol-2-one 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 99-90-1 para-bromoacetophenone 

Relevant academic research and scientific papers

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates

The first copper-catalyzed asymmetric decarboxylative [4 + 1] cycloaddition of propargylic carbamates and sulfur ylides was successfully developed. This strategy led to a series of chiral indolines with synthetically flexible alkyne groups in good yields and with high enantio- and diastereoselectivities (up to 99% yield, 98% ee, and >95:5 dr). A possible mechanism and stereoinduction mode with copper-allenylidenes were proposed as the possible dipolar intermediate.

Gold-catalyzed carbene transfer to alkynes: Access to 2,4-disubstituted furans

Furans of gold: The first example of a gold-catalyzed intermolecular addition of carbon ylides to terminal alkynes is reported (see scheme; DCE=dichloroethane, Tf=trifluoromethanesulfonyl). Subsequent intramolecular trapping of the generated gold carbene completes a formal [3+2] cycloaddition, which represents a novel synthesis of 2,4-disubstituted furans. Copyright

Switching reversibility to irreversibility in glycogen synthase kinase 3 inhibitors: Clues for specific design of new compounds

Development of kinase-targeted therapies for central nervous system (CNS) diseases is a great challenge. Glycogen synthase kinase 3 (GSK-3) offers a great potential for severe CNS unmet diseases, being one of the inhibitors on clinical trials for different tauopathies. Following our hypothesis based on the enhanced reactivity of residue Cys199 in the binding site of GSK-3, we examine here the suitability of phenylhalomethylketones as irreversible inhibitors. Our data confirm that the halomethylketone unit is essential for the inhibitory activity. Moreover, addition of the halomethylketone moiety to reversible inhibitors turned them into irreversible inhibitors with IC50 values in the nanomolar range. Overall, the results point out that these compounds might be useful pharmacological tools to explore physiological and pathological processes related to signaling pathways regulated by GSK-3 opening new avenues for the discovery of novel GSK-3 inhibitors.

Ionic liquid promoted regio- and stereo-selective thiolysis of epoxides-A simple and green approach to β-hydroxy- and β-keto sulfides

A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of ,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled. CSIRO 2007.

Sodium Telluride-Mediated Sulfenylation of α-Halo Carbonyl Compounds with Diphenyl Disulfide

Under mild aprotic conditions α-halo carbonyl compounds react with diphenyl disulfide in the presence of sodium telluride to give the corresponding α-phenylthio derivatives in good to moderate yields.The reaction appears to proceed involving the sulfur-sulfur bond cleavage of diphenyl disulfide by sodium telluride.

Synthesis Using Pyridinium Anhydrobases. Preparation of Indolizine Derivatives

A number of derivatives of indolizine ring system have been prepared from 1-substituted 4,6-diphenyl-2-phenacylidene-1,2-dihydropyridines either by metallation with LDA or acylation and further basic treatment.Similarly, 1-arylmethyl-4,6-diphenyl-2-dicyanomethylene-1,2-dihydropyridines by action of LDA undergo cyclization to the corresponding 2-amino-1-cyano-3-aryl indolizinies.

Extrusion of Sulfur from pyrimidinones

Thermally mediated sulfur extrusion from 4-(phenacylthio)-2(1H)-pyrimidinones occurs rapidly in solution at 125 deg C to yield 4(3H)-(benzoylmethenyl)-2(1H)-pyrimidinones. 4-(Acetonylthio)-2(1H)-pyrimidinone, however, rearranges via an episulfide intermed