28128-12-3

Upstream product

• 53832-62-5 3-anilino-1-butyne 
• 62-53-3 aniline 
• 814-75-5 3-bromo-butanone 
• 61946-78-9 3-phenylimino-2-butanone 
• 513-86-0 3-hydroxy-2-butanon 
• 598-31-2 1-bromoacetone 
• 100-61-8 N-methylaniline 
• 513-85-9 2.3-butanediol 

Downstream Products

• 91-55-4 2,3-dimethylindole 
• 1135586-85-4 (2S,3R)-3-(phenylamino)butan-2-ol 
• 74371-91-8 2,3-dimethyl-1-phenyl-1H-indole 
• 210408-13-2 (1R,2R)-3-(phenylamino)-2-butanol 
• 1342297-64-6 (2R,3S)-3-(phenylamino)butan-2-ol 

Relevant academic research and scientific papers

Synthesis of indoles through acceptorless dehydrogenative coupling catalyzed by nickel on silica-alumina

The high atom-economical formation of indoles from anilines and diols was described with affordable and easy to handle Ni/SiO2-Al2O3. After optimization, 2,3-dimethylindole was isolated with an excellent 98% yield in neat conditions. The scope of the reaction was studied and 13 indoles were isolated in 16–80% yields.

Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes

Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.

Pyrazine Radical Cations as a Catalyst for the Aerobic Oxidation of Amines

An efficient and green synthetic method for the preparation of N,N-disubstituted tetramethylpyrazinium radical cations was developed, which does not require any solvent or strong alkylating agents. The investigation by UV/Vis and electron paramagnetic res

Heterogeneous Ni catalysts for N-alkylation of amines with alcohols

Nickel nanoparticles loaded onto various supports (Ni/MOx) have been prepared and studied for the N-alkylation of amines with alcohols. Among the catalysts, Ni/θ-Al2O3 prepared by in situ H 2-reduction of NiO/θ-Al2O3 shows the highest activity, and it acts as reusable heterogeneous catalyst for the alkylation of anilines and aliphatic amines with various alcohols (benzyl and aliphatic alcohols) under additive free conditions. Primary amines are converted into secondary amines and secondary amines into tertiary amines. For the reaction of aniline with an aliphatic alcohol the catalyst shows higher turnover number (TON) than precious metal-based state-of-the-art catalysts. Mechanistic studies suggest that the reaction proceeds through a hydrogen-borrowing mechanism. The activity of Ni catalysts depends on the nature of support materials; acid-base bifunctional supports give higher activity than basic or acidic supports, indicating that acid-base sites on supports are necessary. The presence of basic (pyridine) or acidic (acetic acid) additive in the solution decreased the activity of Ni/θ-Al2O3, which suggests the cooperation of the acid-base site of θ-Al2O3. For a series of Ni/θ-Al2O3 catalysts with different particle size, the turnover frequency (TOF) per surface Ni increases with decreasing Ni mean particle size, indicating that low-coordinated Ni species and/or metal-support interface are active sites. From these results, we propose that the active site for this reaction is metal-support interface, where low-coordinated Ni0 atoms are adjacent to the acid-base sites of alumina.

Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: An aryne twist of Bischler-Moehlau indole synthesis

Reaction of 2-(trimethylsilyl)aryl triflates 1 with N-aryl-α-amino ketones 2 afforded N-aryl-2,3-disubstituted indoles in good to excellent yields with complete control of the substitution patterns. This methodology allowed for the first time a one-step s

Catalytic enantioselective Amadori-Heyns rearrangement of racemic α-hydroxy ketones with arylamines: Synthesis of optically active α-arylamino ketones

A novel synthesis of optically active α-arylamino ketones through an organocatalytic enantioselective Amadori-Heyns rearrangement is described. The Royal Society of Chemistry 2013.

Convenient, scalable and flexible method for the preparation of imidazolium salts with previously inaccessible substitution patterns

A high yielding and modular approach to N,N′-disubstituted imidazolium salts is described, providing access to substitution patterns that are beyond the reach of established methodology. The Royal Society of Chemistry 2006.

Process for preparing optically active secondary alcohols having nitrogenous or oxygenic functional groups

A process for preparing optically active secondary alcohols of the general formula (3), [wherein R1 is linear lower alkyl, an aromatic ring group, or the like; A is CH2NR2R3 or the like; n is an integer of 0 to 2; and * represents an asymmetric carbon atom] by asymmetrically hydrogenating a ketone compound of the general formula (1) having nitrogenous or oxygen functional group at any of the a-, β- and γ-positions, with selectivity among functional groups by the use of a ruthenium/optically active bidentate phosphine/diamine complex as the catalyst in the presence of hydrogen alone or together with a base. The optically active secondary alcohols obtained by the process are useful as drugs and intermediates for the preparation of drugs.

Reduction of N-substituted 1-acetyl- and 1-benzoyl-ethanimines

The reduction of N-substituted 1-acetyl- and 1-benzoyl-ethanimines leads to aminoketones or aminoalcohols, depending upon the nature of the reducing agent employed.The reduction to aminoalcohols affords diastereomeric mixtures.A stereochemical pathway for