27376-59-6

Upstream product

• 637-59-2 1-Bromo-3-phenylpropane 
• 103-49-1 dibenzylamine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 122-97-4 3-Phenyl-1-propanol 
• 104-54-1 3-Phenylpropenol 
• 3271-81-6 hydrocinnamanilide 
• 55334-41-3 3-phenyl-N,N-bis(phenylmethyl)-2-propenamide 
• 180747-56-2 (N,N)-dibenzyl-3-phenylpropanamide 
• 645-45-4 hydrocinnamic acid chloride 
• 104-53-0 3-phenyl-propionaldehyde 
• 193475-95-5 N,N-dibenzyl-N-(3-phenylprop-1-enyl)amine 

Downstream Products

• 30684-05-0 3-phenylpropylamine hydrochloride 

Relevant academic research and scientific papers

One-Pot Controlled Reduction of Conjugated Amides by Sequential Double Hydrosilylation Catalyzed by an Iridium(III) Metallacycle

A single and accessible cationic iridiumIII metallacycle effectively catalyzes the one-pot sequential double hydrosilylation of challenging α,β-unsaturated secondary and tertiary amides to afford, in a controlled and straightforward way, the co

Efficient and Selective Hydrosilylation of Secondary and Tertiary Amides Catalyzed by an Iridium(III) Metallacycle: Development and Mechanistic Investigation

Readily accessible cationic IrIII metallacycles catalyze efficiently the chemoselective hydrosilylation of tertiary and secondary amides to amines. The catalyst described herein operates at low loadings using inexpensive 1,1,3,3-tetramethyldisiloxane and allows fast reactions with high yields, selectivities, and turnover numbers. A transient iminium intermediate has been observed for the first time by using mass spectrometry, and the activation of the catalyst and the silane reagent have been studied by using DFT calculations. These fundamental insights support the present and future improvements of IrIII metallacycles through proper ligand modifications and enable further broad applications of catalysts based on metallacycles.

Nickel-Catalyzed Reduction of Secondary and Tertiary Amides

The nickel-catalyzed reduction of secondary and tertiary amides to give amine products is reported. The transformation is tolerant of extensive variation with respect to the amide substrate, proceeds in the presence of esters and epimerizable stereocenters, and can be used to achieve the reduction of lactams. Moreover, this methodology provides a simple tactic for accessing medicinally relevant α-deuterated amines.

Carboxamides as N-Alkylating Reagents of Secondary Amines in Indium-Catalyzed Reductive Amination with a Hydrosilane

A method for the catalytic reductive N-alkylation of amines by using secondary amides as the alkyl source was developed. A versatile type of carboxamide functioned as an N-alkylation reagent in the presence of an indium(III) catalyst and a hydrosilane to provide alkylated tertiary amines efficiently. This amide-based catalytic N-alkylation strategy is considered to be a highly useful protocol to access unsymmetrical tertiary amines.

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.

Development and mechanistic investigation of a highly efficient iridium(V) silyl complex for the reduction of tertiary amides to amines

The cationic Ir(III) acetone complex (POCOP)Ir(H)2(acetone) + (POCOP = 2,6-bis(di-tert-butylphosphinito)phenyl) was shown to catalyze the reduction of a variety of tertiary amides to amines using diethylsilane as reductant. Mechanistic studies established that a minor species generated in the reaction, the neutral silyl trihydride Ir(V) complex (POCOP)IrH3(SiEt2H), was the catalytically active species. High concentrations of this species could be conveniently generated by treatment of readily available (POCOP)IrHCl with tert-butoxide in the presence of Et2SiH2 under H2. Thus, using this mixture in the presence of a trialkylammonium salt, a wide array of tertiary amides, including extremely bulky substrates, are rapidly and quantitatively reduced to tertiary amines under mild conditions with low catalyst loading. A detailed mechanistic study has been carried out and intermediates identified. In brief, (POCOP)IrH3(SiEt2H) reduces the amide to the hemiaminal silyl ether that, in the presence of a trialkylammonium salt, is ionized to the iminium ion, which is then reduced to the tertiary amine by Et 2SiH2. Good functional group compatibility is demonstrated, and a high catalyst stability has provided turnover numbers as high as 10 000.

Reductive cleavage of amides to alcohols and amines catalyzed by well-defined bimetallic molybdenum complexes

Triple bonds do it! The molybdenum-catalyzed Ci-N bond cleavage of organic amides with hydrosilanes to produce alcohols and amines has been investigated. This work complements previously established protocols that lead to the cleavage of the Ci-O bond. Modified triply bonded dimolybdenum(III) alkoxides have been found to be crucial for tuning the selectivity to Ci-N bond cleavage (see figure). Copyright

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.

A convenient and general iron-catalyzed reduction of amides to amines

While the iron is hot: The first general and efficient iron-catalyzed reduction of secondary and tertiary amides into amines using polymethylhydrosiloxane (PMHS) has been developed (see scheme).

Highly chemoselective metal-free reduction of tertiary amides

This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines. Hantzsch ester is used as a mild reducing agent for the reduction of trifluoromethanesulfonic anhydride activated amides providing the tertiary amines with high functional group tolerance. Copyright