33500-61-7

Upstream product

• 74-88-4 methyl iodide 
• 102-04-5 1,3-Diphenylpropanone 
• 140902-14-3 Trimethyl-{2-phenyl-1-[1-phenyl-meth-(Z)-ylidene]-propoxy}-silane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 108-90-7 chlorobenzene 
• 96-22-0 pentan-3-one 
• 1114455-30-9 4-methyl-2,4-diphenyl-nonane-3,5-dione 
• 109-72-8 n-butyllithium 
• 1114455-07-0 Z-3-methyl-3-phenyl-4-(1-phenyl-ethylidene)-oxetan-2-one 
• 917-54-4 methyllithium 
• 811-49-4 ethyllithium 
• 591-51-5 phenyllithium 
• 67-56-1 methanol 
• 108-86-1 bromobenzene 

Downstream Products

• 1857-74-5 2,3-diphenylbutane 
• 34713-70-7 2-Phenylpropanal 
• 2348-51-8 1-phenylethyl radical 
• 84175-25-7 α-methylphenacetyl radical 
• 100-42-5 styrene 
• 100-41-4 ethylbenzene 
• 20819-55-0 ethylbenzene peroxide radical 
• 33484-57-0 3-Methyl-2,4-diphenyl-pentan 

Relevant academic research and scientific papers

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

N-heterocyclic carbene-palladium-imine complex catalyzed α-arylation of ketones with aryl and heteroaryl chlorides under air atmosphere

A new structure of saturated ring skeleton monoligated NHC-Pd-Imine complex was easily synthesized and unambiguously confirmed by X-ray single crystal diffraction. It was found to be an efficient and air-stable catalyst for the α-arylation of ketones. The reaction could be operated in air without any negative effect. Non-activated aryl and heteroaryl chlorides have been successfully applied in the reaction with only 0.5 mol% catalyst loadings under air atmosphere. Excellent to good product yields were afforded.

Direct Synthesis of Mono-α-arylated Ketones from Alcohols and Olefins via Ni-Catalyzed Oxidative Cross-Coupling

Controlled synthesis of α-monoarylated ketones is significant yet challenging due to the site-selectivity issues and nonproductive overarylation reactions. Herein, we reported the direct synthesis of α-arylated ketones enabled by Ni-catalyzed dehydrogenative cross-coupling reaction cascade between alcohols and olefins. The use of readily available and cost-effective alcohols and olefins provides a straightforward access to monoarylated ketones in good yields with exclusive selectivity without using any advanced synthetic intermediates.

NCN-Pincer palladium complexes immobilized on MCM-41 molecular sieve: Application in Α-arylation reactions

Aromatic para-functionalized NCN pincer compounds tethered to a triethoxysilane moiety through a carbamate linkage were immobilized on ordered MCM-41 molecular sieve using a grafting process. The acquired immobilized organometallic pincer complexes were synthesized in high yields with no complex degradation and characterized by IR sprctroscopy, elemental content analysis. Nitrogen physisorption, XRD and TEM revealed that the mesoporous structure was retained during the immobilization process. The hybrid materials were applied as Lewis acid catalysts in the α-arylation reaction between aryl ketones and aryl halides, with the yield up to 95%. The tendency to form mono- or di-arylated products was investigated and the catalyst could be easily recovered and reused in five runs without a significant loss in its activity.

C -Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts

A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of symmetric dialkyl ketones with aryl chlorides

N-Heterocyclic carbene-palladium(II)-1-methylimidazole [NHC-Pd(II)-Im] complex 1 showed efficient catalytic activity toward α-arylation of symmetric dialkyl ketones under mild conditions. It was found that the ratio of aryl chlorides and ketones drastical

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed a-arylation of symmetric dialkyl ketones with aryl chlorides

N-Heterocyclic carbene-palladium(II)-1-methylimidazole [NHC-Pd(II)-Im] complex 1 showed efficient catalytic activity toward α-arylation of symmetric dialkyl ketones under mild conditions. It was found that the ratio of aryl chlorides and ketones drastical

N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of symmetric dialkyl ketones with aryl chlorides

N-Heterocyclic carbene-palladium(II)-1-methylimidazole [NHC-Pd(II)-Im] complex 1 showed efficient catalytic activity toward α-arylation of symmetric dialkyl ketones under mild conditions. It was found that the ratio of aryl chlorides and ketones drastical

Nucleophilic reactivity of a copper(II)-superoxide complex

Metal-bound superoxide intermediates are often implicated as electrophilic oxidants in dioxygen-activating metalloenzymes. In the nonheme iron α-ketoglutarate dependent oxygenases and pterin-dependent hydroxylases, however, FeIII-superoxide intermediates are postulated to react by nucleophilic attack on electrophilic carbon atoms. By reacting a Cu II-superoxide complex (1) with acyl chloride substrates, we have found that a metal-superoxide complex can be a very reactive nucleophile. Furthermore, 1 was found to be an efficient nucleophilic deformylating reagent, capable of Baeyer-Villiger oxidation of a number of aldehyde substrates. The observed nucleophilic chemistry represents a new domain for metal-superoxide reactivity. Our observations provide support for the postulated role of metal-superoxide intermediates in nonheme iron α-ketoglutarate dependent and pterin-dependent enzymes. Nucleophilic superoxide: A copper(II)-superoxide complex has been found to be a highly reactive nucleophile. The complex reacts readily with certain electrophiles and is capable of the nucleophilic deformylation of electron-rich aldehydes (Baeyer-Villiger oxidation). These observations provide experimental support for the postulated nucleophilic reactivity of metal-superoxide intermediates in the catalytic cycles of certain nonheme iron enzymes.

Iridium-catalyzed selective α-methylation of ketones with methanol

Iridium-catalyzed selective α-dimethylation and α-methylation of ketones or phenylacetonitriles, using methanol as the methylating agent, were achieved. In addition, three-component cross α-methyl-alkylation was successfully performed using methyl ketones with methanol and primary alcohols with long-chain alkyl groups. This method provides a very convenient direct route to α-methylated ketones, using methanol.