73627-36-8

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 78-84-2 isobutyraldehyde 
• 54016-70-5 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide 

Downstream Products

• 1293372-48-1 (4S,5R)-4,5-bis-(4-trifluoromethylphenyl)-[1,2,3]oxathiazolidine 2,2-dioxide 
• 1293372-34-5 4,5-bis-(4-trifluoromethylphenyl)-5H-[1,2,3]oxathiazole 2,2-dioxide 
• 143547-12-0 (3-{2-[4,5-Bis-(4-trifluoromethyl-phenyl)-oxazol-2-yl]-ethyl}-phenoxy)-acetic acid 
• 73790-20-2 4,4'-bis(trifluoromethyl)benzil 
• 73627-37-9 4,5-Bis-(4-trifluoromethyl-phenyl)-1,3-dihydro-imidazole-2-thione 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling

The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular-benzoin, intramolecular-benzoin, intermolecular-Stetter and intramolecular-Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent-minimised conditions.

Generation and reactivity of phenylhydroxycarbenes in solution

We provide evidence for the first successful generation of phenylhydroxycarbene and 4-trifluoromethylphenylhydroxycarbene in solution. The carbene tautomers of the corresponding benzaldehyde derivatives had been prepared under cryogenic matrix-isolation conditions before but their reactivity, apart from a prototypical quantum mechanical tunneling [1,2]-H-shift reaction, had not been studied. Here our strategy is to employ suitable carbene precursors for the McFadyen–Stevens reaction, to generate the parent and the para-CF3-substituted phenylhydroxycarbenes, and to react them with benzaldehyde or acetone in a highly facile, allowed six-electron carbonyl-ene reaction toward the corresponding α-hydroxy ketones. Our findings are supported by computations at the DLPNO-CCSD(T)/cc-pVQZ//B3LYP/def2-TZVP level of theory.

COMPOUNDS AND USES THEREOF IN THE TREATMENT OF CANCERS AND OTHER MEDICAL CONDITIONS

There are provided compounds, their preparation and their use in the treatment of medical conditions including cancers and immune disorders.

Self-supported N-heterocyclic carbenes and their use as organocatalysts

The study of N-heterocyclic carbenes (NHCs) as organocatalysts has proliferated in recent years, and they have been found to be useful in a variety of reactions. In an attempt to further expand their utility and to study their recyclability, we designed and synthesized a series of self-supported NHCs in which the catalytic carbene groups form part of a densely functionalized polymer backbone, and studied them as organocatalysts. Of the self-Supported NHCs examined, a benzimidazole derived polymer with flexible linkers connecting the catalytic groups was found to be the most efficient organocatalyst in a model benzoin condensation reaction, and thus it was used in a variety of such reactions, including some involving catalyst recycling. Furthermore, it was also used to catalyze a set of redox esterification reactions involving conjugated unsaturated aldehydes. In all of these reactions the catalyst afforded good yield of the desired product and its polymeric nature facilitated product purification.

Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

We found that chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio. Moreover, we observed the persistent catalytic activity of the homogeneous NHC catalyst in a solution due to N

Poly(4-vinylimidazolium) iodides: A highly recyclable organocatalyst precursor for benzoin condensation reaction

The development of highly efficient, recyclable poly(4-vinylimidazolium) iodides (2) for the benzoin condensation reaction under mild reaction conditions is discussed: poly(4-vinyl N-heterocyclic carbene)s (3) obtained from 2 showed higher catalytic activity than monomeric 4-vinyl N-heterocyclic carbene and could be successfully recovered and reused over seven times without loss of performance. the Partner Organisations 2014.

Design, synthesis and biological evaluation of 2, 4, 5-triphenylimidazole derivatives with preliminary SAR

A series of N1-substituted 2,4,5-triphenyl imidazole derivatives was designed, synthesized and evaluated for their p53-MDM2 binding inhibitory activities and anti-proliferative activities in vitro against four human cancer cell lines (PC3, KB, A549 and HCT116). Although logical evaluation revealed weak p53-MDM2 binding inhibitory activities, most of the obtained molecules displayed moderate to potent cytotoxicities against tested cell lines. As a potential lead compound for further optimization, compound 9c was evaluated as the most potent compound against four cell lines and could induce cell cycle arrest at G2/M phase. The binding mode of compound 9f and MDM2 was further studied by docking analysis and the unexpected interaction mode revealed that this series of compounds may take part into a different binding modes as the lead compound Such as Nutlin, which could induce a different mechanism in cancer therapy.

Asymmetric benzoin condensation promoted by chiral triazolium precatalyst bearing a pyridine moiety

Chiral triazolium salts bearing a pyridine ring were developed as N-heterocyclic carbene precursors. In the presence of the chiral triazolium salt and a base, the catalytic asymmetric benzoin condensation proceeded to afford the product in high level of chemical yield and enantioselectivity. A wide range of aromatic aldehydes were applicable to this reaction.

N-heterocyclic carbene-catalyzed annulation of α-cyano-1,4-diketones with ynals

In this paper, the first stereoselective annulation reaction between r-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

N-heterocyclic carbene-catalyzed annulation of α-cyano-1,4-diketones with ynals

In this paper, the first stereoselective annulation reaction between r-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.