24997-83-9

Upstream product

• 127302-02-7 Benzyl-hexyl-phenethyl-amine 
• 142-92-7 1-hexyl acetate 
• 64-04-0 phenethylamine 
• 81745-81-5 ⁿhexylzinc chloride 
• 139158-05-7 2-methyl-1-phenethylpiperidine 
• 766-08-5 methylphenylsilane 
• 103-63-9 1-phenyl-2-bromoethane 
• 109-05-7 2-Methylpiperidin 
• 111-26-2 hexan-1-amine 
• 536-74-3 phenylacetylene 
• 6125-24-2 2-Phenylnitroethane 
• 111-27-3 hexan-1-ol 
• 140-29-4 phenylacetonitrile 
• 100-42-5 styrene 

Downstream Products

• 549532-36-7 ethyl (2S)-2-ethoxy-3-(4-{2-[hexyl-(2-phenylethyl)amino]-2-oxoethoxy}phenyl)propanoate 

Relevant academic research and scientific papers

Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines

Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.

Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.

Direct Reductive N-Functionalization of Aliphatic Nitro Compounds

The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic amination of zinc organyls.

Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology

Using a simple amino amide ligand, ruthenium-catalyzed one-pot alkylation of primary and secondary amines with simple alcohols was carried out under a wide range of conditions. Using the alcohol as solvent, alkylation was achieved under mild conditions, even as low as room temperature. Reactions occurred with high conversion and selectivity in many cases. Reactions can also be carried out at high temperatures in organic solvent with high selectivity using stoichiometric amounts of the alcohol.

Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions

An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2]2, with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.

Pt/C catalysed direct reductive amination of nitriles with primary amines in a continuous flow multichannel microreactor

Aliphatic and aromatic secondary amines were synthesised selectively by one pot reductive amination of nitriles with primary amines using Pt/C (3% by weight) catalyst in a continuous flow multichannel microreactor. Molecular hydrogen was used as a clean reducing agent at moderate reaction conditions. The Royal Society of Chemistry 2013.

When bigger is better: Intermolecular hydrofunctionalizations of activated alkenes catalyzed by heteroleptic alkaline earth complexes

New alkaline-earth amido complexes catalyze the regioselective intermolecular hydroamination (see scheme; Ae=alkaline earth) and hydrophosphination of styrene and isoprene with unprecedented activities. The catalytic performances increased linearly with the size of the metal. Copyright

One-pot reductive amination of aldehydes and ketones with α-picoline-borane in methanol, in water, and in neat conditions

A one-pot reductive amination of aldehydes and ketones with amines using α-picoline-borane as a reducing agent is described. The reaction has been carried out in MeOH, in H2O, and in neat conditions in the presence of small amounts of AcOH. This is a highly efficient and mild procedure that is applicable for a wide variety of substrates. In particular, this is the first successful demonstration that this type of reaction can be carried out in water and in neat conditions.

Radical cyclisations of imines and hydrazones

Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.

ALKYLAMINOMETHYLATION D'ORGANOMAGNESIENS.

The organomagnesium compound RMgX is converted, in two steps, into the secondary amine R-CH2-NH-R1 (R1=CH3 or alkyl).