4393-08-2

Upstream product

• 111-25-1 1-bromo-hexane 
• 100-46-9 benzylamine 
• 143-16-8 dihexylamine 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 111-27-3 hexan-1-ol 
• 622-79-7 benzyl azide 
• 111-87-5 octanol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 143-16-8 dihexylamine 

Relevant academic research and scientific papers

Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines

Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.

Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions

Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.

Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation

A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.

Mild nonepimerizing N -alkylation of amines by alcohols without transition metals

A one-pot two-step sequence involving an oxidation/imine-iminium formation/reduction allowed the N-alkylation of amines by alcohols without any epimerization when optically active alcohols and amines are involved in the process.

Ruthenium-catalyzed formation of tertiary amines from nitriles and alcohols

A ruthenium-catalyzed tertiary-amine formation was developed using the borrowing hydrogen strategy. Various tertiary amines were obtained efficiently from nitriles and primary alcohols. Two possible pathways were found for the tertiaryamine formation under RuCl3/dppf catalytic conditions. The nitriles mainly act as a nitrogen source in this kind of transformation.

First example of direct reductive amination of aldehydes with primary and secondary amines catalyzed by water-soluble transition metal catalysts

An unprecedented efficient and highly selective direct reductive amination of aldehydes with primary and secondary amines in water using gaseous hydrogen and water-soluble catalysts is developed. The catalytic system formed in situ from Pd(PhCN)2Cl2 and 2,2′-biquinoline-4,4′-dicarboxylic acid dipotassium salt (BQC), allows full conversion of aldehydes and the formation of desired alkylated amines with excellent yields and selectivities. The catalytic system is stable and can be recycled and reused three times without loss of activity.

Gas-phase selective N-alkylation of amines with alcohols over γ- alumina

Gas-phase conditions were successfully used for fine chemistry, in the N-alkylation of amines with alcohols as alkylating agents and γ-alumina as a catalyst. The method is also suitable for chiral compounds.