Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Efficient three-component Strecker reaction of aldehydes/ketones via NHC-amidate palladium(II) complex catalysis.

ABSTRACT: A simple and efficient one-pot, three-component method has been developed for the synthesis of alpha-aminonitriles. This Strecker reaction is applicable for aldehydes and ketones with aliphatic or aromatic amines and trimethylsilyl cyanide in the presence of a palladium Lewis acid catalyst in dichloromethane solvent at room temperature.

SUBMITTER: Jarusiewicz J

PROVIDER: S-EPMC2713785 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Efficient three-component Strecker reaction of aldehydes/ketones via NHC-amidate palladium(II) complex catalysis.

Jarusiewicz Jamie J Choe Yvonne Y Yoo Kyung Soo KS Park Chan Pil CP Jung Kyung Woon KW

The Journal of organic chemistry 20090401 7

A simple and efficient one-pot, three-component method has been developed for the synthesis of alpha-aminonitriles. This Strecker reaction is applicable for aldehydes and ketones with aliphatic or aromatic amines and trimethylsilyl cyanide in the presence of a palladium Lewis acid catalyst in dichloromethane solvent at room temperature. ...[more]

PMID: 19265413

Similar Datasets

Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Project description:Chiral dimeric tridentate NHC-amidate-alkoxide palladium(II) complexes, 3a and 3b, effected oxidative boron Heck-type reactions of aryl boronic acids with both acyclic and cyclic alkenes at room temperature to afford the corresponding coupling products with high enantioselectivities. The high degree of enantioselection, far superior to existing methods, stems from differences in the nonbonding interactions in the proposed transition states, due to the influence from bulky substituents of the alkene substrates and the "counter axial groups" of the palladium(II) catalysts.

| S-EPMC2798920 | biostudies-literature

Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs.

Project description:The synthesis of alpha-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the alpha-aminonitrile product by varying the nature of the fluorinated ketones. Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper catalyst and the solvent system (suitable metal triflates as a catalyst and dichloromethane as a solvent) plays the key role in the direct Strecker reactions of ketones.

| S-EPMC1820647 | biostudies-literature

Building a Green, Robust, and Efficient Bi-MOF Heterogeneous Catalyst for the Strecker Reaction of Ketones.

Project description:In this work, we present the new [Bi14(μ3-O)9(μ4-O)2(μ3-OH)5(3,5-DSB)5(H2O)3]·7H2O, BiPF-4 (bismuth polymeric framework─4) MOF, its microwave hydrothermal synthesis, as well as its behavior as a heterogeneous catalyst in the multicomponent organic Strecker reaction. The BiPF-4 material shows a three-dimensional (3D) framework formed by peculiar inorganic oxo-hydroxo-bismutate layers connected among them through the 3,5-dsb (3,5-disulfobenzoic acid) linker. These two-dimensional (2D) layers, built by junctions of Bi7 polyhedra SBU, provide the material of many Lewis acid catalytic sites because of the mixing in the metal coordination number. BiPF-4 is a highly robust, green, and stable material that demonstrates an excellent heterogeneous catalytic activity in the multicomponent Strecker reaction of ketones carried out in one-pot synthesis, bringing a reliable platform of novel green materials based on nontoxic and abundant metal sources such as bismuth.

| S-EPMC9115759 | biostudies-literature

Practical Synthesis of C-1 Deuterated Aldehydes Enabled by NHC Catalysis.

Project description:The recent surge in applications of deuterated pharmaceutical agents has created an urgent demand for synthetic methods that efficiently generate deuterated building blocks. Here we show that N-heterocyclic carbenes (NHC) promote a reversible hydrogen-deuterium exchange (HDE) reaction with simple aldehydes, which leads to a practical approach to synthetically valuable C-1 deuterated aldehydes. The reactivity of the well-established NHC catalysed formation of Breslow intermediates from aldehydes is reengineered to overcome the overwhelmingly kinetically favorable, irreversible benzoin condensation reaction and achieve the critical reversibility to drive the formation of desired deuterated products when an excess of D2O is employed. Notably, this operationally simple and cost-effective protocol serves as a general and truly practical approach to all types of 1-D-aldehydes including aryl, -alkyl and -alkenyl aldehydes and enables chemoselective late-stage deuterium incorporation into complex, native therapeutic agents and natural products with uniformly high levels (>95%) of deuterium incorporation for a total of 104 substrates tested.

| S-EPMC8008838 | biostudies-literature

Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Project description:We report the palladium-catalyzed, pyrrolidine-mediated α-benzylation of enamines generated from aldehydes and ketones. The method allows for direct coupling of medicinally relevant coumarin moieties with aldehydes and ketones in good yield under mild conditions. The reaction is believed to proceed via a Pd-π-benzyl complex generated from (coumarinyl)methyl acetates.

| S-EPMC3443958 | biostudies-literature

Cooperative NHC and Photoredox Catalysis for the Synthesis of β-Trifluoromethylated Alkyl Aryl Ketones.

Project description:Despite the great potential of radical chemistry in organic synthesis, N-heterocyclic carbene (NHC)-catalyzed reactions involving radical intermediates are not well explored. This communication reports the three-component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3 SO2 Na) to give various β-trifluoromethylated alkyl aryl ketones with good functional group tolerance in moderate to high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross coupling of ketyl radicals with benzylic C-radicals. The ketyl radicals are generated via SET reduction of in situ formed acylazolium ions whereas the benzylic radicals derive from trifluoromethyl radical addition onto styrenes.

| S-EPMC7693039 | biostudies-literature

H-D exchange in deuterated trifluoroacetic acid via ligand-directed NHC-palladium catalysis: a powerful method for deuteration of aromatic ketones, amides, and amino acids.

Project description:A method has been developed for one-step ortho-selective ligand-directed H-D exchange, accompanied in some cases by concurrent acid-catalyzed electrophilic deuteration. This method is effective for deuteration of aromatic substrates ranging from ketones to amides and amino acids, including compounds of biological and pharmaceutical interest such as acetaminophen and edaravone. Use of a palladium catalyst featuring an NHC ligand is critical for the observed reactivity. Experimental evidence strongly suggests that palladium facilitates C-H activation of the aromatic substrates, a mechanism seldom observed under strongly acidic conditions. 2015 Elsevier Ltd. All rights reserved.

| S-EPMC4610012 | biostudies-literature

Palladium/Rhodium Cooperative Catalysis for the Production of Aryl Aldehydes and Their Deuterated Analogues Using the Water-Gas Shift Reaction.

Project description:A novel Pd/Rh dual-metallic cooperative catalytic process has been developed to effect the reductive carbonylation of aryl halides in moderate to good yield. In this reaction, water is the hydride source, and CO serves both as the carbonyl source and the terminal reductant through the water-gas shift reaction. The catalytic generation of the Rh hydride allows for the selective formation of highly hindered aryl aldehydes that are inaccessible through previously reported reductive carbonylation protocols. Moreover, aldehydes with deuterated formyl groups can be efficiently and selectively synthesized using D2 O as a cost-effective deuterium source without the need for presynthesizing the aldehyde.

| S-EPMC6173325 | biostudies-literature

Palladium(0) NHC complexes: a new avenue to highly efficient phosphorescence.

Project description:We report the first examples of highly luminescent di-coordinated Pd(0) complexes. Five complexes of the form [Pd(L)(L')] were synthesized, where L = IPr, SIPr or IPr* NHC ligands and L' = PCy3, or IPr and SIPr NHC ligands. The photophysical properties of these complexes were determined in degassed toluene solution and in the solid state and contrasted to the poorly luminescent reference complex [Pd(IPr)(PPh3)]. Organic light-emitting diodes were successfully fabricated but attained external quantum efficiencies of between 0.3 and 0.7%.

| S-EPMC5657412 | biostudies-literature

Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Project description:Synergistic palladium and enamine catalysis was explored to promote ketone addition to unactivated olefins. A secondary amine-based organocatalyst was identified as the optimal co-catalyst for the directed Pd-catalyzed alkene activation. Furthermore, asymmetric hydrocarbon functionalization of unactivated alkenes was also achieved with good to excellent yield (up to 96% yields) and stereoselectivity (up to 96% ee). This strategy presented an efficient approach to prepare α-branched ketone derivatives under mild conditions.

| S-EPMC6677245 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data