15429-10-4

Upstream product

• 104-86-9 4-chlorobenzylamine 
• 100-51-6 benzyl alcohol 
• 104-88-1 4-chlorobenzaldehyde 
• 103-49-1 dibenzylamine 
• 98-88-4 benzoyl chloride 
• 27032-10-6 4-chlorobenzyl azide 
• 1426958-17-9 N,N-dibenzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-amine 
• 100-46-9 benzylamine 
• 873-76-7 para-Chlorobenzyl alcohol 
• 55-21-0 benzamide 
• 1485-70-7 N-benzylbenzamide 
• 122-01-0 4-chloro-benzoyl chloride 
• 622-95-7 4-chlorobenzyl bromide 
• 7461-37-2 N,N-dibenzyl-4-chlorobenzamide 

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.

Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines

Homoleptic lanthanide complex Y[N(TMS)2]3 is an efficient homogeneous catalyst for the hydroboration reduction of secondary amides and tertiary amides to corresponding amines. A series of amides containing different functional groups such as cyano, nitro, and vinyl groups were found to be well-tolerated. This transformation has also been nicely applied to the synthesis of indoles and piribedil. Detailed isotopic labeling experiments, control experiments, and kinetic studies provided cumulative evidence to elucidate the reaction mechanism.

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.

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).

Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism

An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.

Scalable synthesis of secondary and tertiary amines by heterogeneous Pt-Sn/γ-Al2O3catalyzed N-alkylation of amines with alcohols

Synthesis of secondary and tertiary amines has been efficiently realized from the N-alkylation of amines with alcohols by means of heterogeneous bimetallic Pt-Sn/γ-Al2O3catalyst (0.5?wt % Pt, molar ratio Pt:Sn?=?1:3) through a borrowing hydrogen strategy. The Pt-Sn/γ-Al2O3catalyst has exhibited very high catalytic activity towards a wide range of amines and alcohols, and can be conveniently recycled without Pt metal leaching. The present protocol was applied for the synthesis of N-phenylbenzylamine in 96% isolated yield from aniline and benzyl alcohol on a 2.1?kg scale of the substrates, demonstrating its potential applicability for higher-order amine synthesis.

Efficient metal-free hydrosilylation of tertiary, secondary and primary amides to amines

Hydrosilylation of secondary and tertiary amides to amines is described using catalytic amounts of B(C6F5)3. The organic catalyst enables the reduction of amides with cost-efficient, non-toxic and air stable PMHS and TMDS hydrosilanes. The methodology was successfully extended to the more challenging reduction of primary amides.

Cobalt carbonyl-based catalyst for hydrosilylation of carboxamides

The cobalt carbonyl [Co2(CO)8] complex is employed as a useful catalyst for the reduction of tertiary amides to the corresponding tertiary amines using 1,1,3,3-tetramethyldisiloxane (TMDS) and poly(methylhydrosiloxane) (PMHS) as silane reagents under thermal (100 °C) or photo-assisted conditions (UV, 350 nm at room temperature). Of particular interest, a low catalytic amount (0.5 mol%) of [Co2(CO)8] is used to perform the reaction with 2.2 equiv. of PMHS at 100 °C for 3 h. This reaction is the first example of a cobalt-catalyzed hydrosilylation of amides. Copyright

Coordination chemistry and catalytic activity of ruthenium(II) complexes containing a phospha-macrocyclic ligand

Substitution of [RuCl2(CO)3(THF)], [RuCl 2(dmso)4] and [RuCl2(PPh3) 3] with a macrocyclic ligand, 2,3,4,5,6,7,8,9-octahydro-1,9-diphenyl- 1H-5,1,9-benzazadiphosphacyclo undecine (11-P2NH), provided [Ru(11-P2NH)Cl2(CO)] (3), [Ru(11-P2NH)Cl 2(dmso)] (4) and [Ru(11-P2NH)Cl2(CH 3CN)] (5), respectively. These complexes were characterized by elemental analyses as well as NMR spectroscopy. The structure of 3 was further confirmed by X-ray diffraction analysis. The octahedral geometry around the ruthenium center is in agreement with the Werner's "coordination" bonding concepts. The chelate rings of the macrocycle toward Ru(II) center adopting into chair conformations were revealed. Furthermore, these ruthenium complexes were found to be active for N-alkylation of dibenzylamine with alcohols.

Preparation of secondary and tertiary amines from nitroarenes and alcohols

Various secondary amines were obtained selectively from the reaction of nitroarenes with primary alcohols in the presence of ruthenium(ii) complexes having phosphine-amine ligands as the catalyst. Secondary amines could be further alkylated with a primary alcohol using the same catalyst, but different conditions.