Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot synthesis of amides via the oxidative amidation of aldehydes and amines catalyzed by a copper-MOF.

ABSTRACT: An efficient method for the oxidative amidation of aldehydes with primary aromatic and aliphatic amines has been developed for the synthesis of a wide variety of amides using inexpensive Cu₂(BDC)₂DABCO (Cu-metal-organic framework [MOF]) as a recyclable heterogeneous catalyst, and N-chlorosuccinimide and aqueous tert-butyl hydroperoxide as oxidants in acetonitrile. This amidation reaction is operationally straightforward and provides secondary amides in good yields in most cases, utilizing inexpensive and readily available reagents under mild conditions.

SUBMITTER: Jamalifard S

PROVIDER: S-EPMC9067141 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-pot synthesis of amides via the oxidative amidation of aldehydes and amines catalyzed by a copper-MOF.

Jamalifard Samira S Mokhtari Javad J Mirjafary Zohreh Z

RSC advances 20190723 39

An efficient method for the oxidative amidation of aldehydes with primary aromatic and aliphatic amines has been developed for the synthesis of a wide variety of amides using inexpensive Cu2(BDC)2DABCO (Cu-metal-organic framework [MOF]) as a recyclable heterogeneous catalyst, and N-chlorosuccinimide and aqueous tert-butyl hydroperoxide as oxidants in acetonitrile. This amidation reaction is operationally straightforward and provides secondary amides in good yi ...[more]

PMID: 35519471

Similar Datasets

Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides.

Project description:The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.

| S-EPMC5954618 | biostudies-literature

Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: synthesis of primary amides.

Project description:A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.

| S-EPMC9047451 | biostudies-literature

Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines.

Project description:A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.

| S-EPMC5273591 | biostudies-literature

Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl4.

Project description:A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl4 is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excellent yields and high purity. The reaction proceeds with low yields when both the carboxylic acid and the amine are sterically hindered. The process takes place with nearly complete preservation of the stereochemical integrity of chiral substrates.

| S-EPMC5602818 | biostudies-literature

One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.

Project description:A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor-acceptor cyclopropanes and subsequent in situ reduction of enamine (imine) intermediates.

| S-EPMC4749319 | biostudies-literature

Copper-Catalyzed Dehydrogenative Amidation of Light Alkanes.

Project description:The functionalization of C-H bonds in light alkanes, particularly to form C-N bonds, remains a challenge. We report the dehydrogenative coupling of amides with C1-C4 hydrocarbons to form N-alkyl amide products with tBuOOtBu as oxidant, and a copper complex of a phenanthroline-type ligand as catalyst. The reactions occurred in good yields in benzene or supercritical carbon dioxide as solvents. This strategy allowed for the determination of the relative reactivity of these alkane C-H bonds toward this amination process and showed, in contrast to prior work with larger alkanes, that the reactivity correlated with bond dissociation energies.

| S-EPMC8457245 | biostudies-literature

Zirconium-catalyzed one-pot synthesis of benzoxazoles using reaction of catechols, aldehydes and ammonium acetate.

Project description:In this study, an efficient method for the synthesis of benzoxazoles by coupling catechols, aldehydes and ammonium acetate using ZrCl4 as catalyst in ethanol is reported. A wide range of benzoxazoles (59 examples) are smoothly produced in high yields (up to 97%). Other advantages of the method include large-scale synthesis and the use of oxygen as an oxidant. The mild reaction conditions allowed late-stage functionalization, facilitating access to several derivatives with biologically relevant structures such as β-lactam and quinoline heterocycles.

| S-EPMC11522672 | biostudies-literature

Direct synthesis of amides and imines by dehydrogenative homo or cross-coupling of amines and alcohols catalyzed by Cu-MOF.

Project description:Oxidative dehydrogenative homo-coupling of amines to imines and cross-coupling of amines with alcohols to amides was achieved with high to moderate yields at room temperature in THF using Cu-MOF as an efficient and recyclable heterogeneous catalyst under mild conditions. Different primary benzyl amines and alcohols could be utilized for the synthesis of a wide variety of amides and imines. The Cu-MOF catalyst could be recycled and reused four times without loss of catalytic activity.

| S-EPMC9034032 | biostudies-literature

N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system.

Project description:The coupling of arylboroxines with a variety of amines, amides, imides and sulfonamides catalyzed by a copper salt/EtOH system has been developed. In the absence of a base or additive the corresponding N-arylation products were obtained in moderate to excellent yields.

| S-EPMC2587945 | biostudies-literature

One-pot aminobenzylation of aldehydes with toluenes.

Project description:Amines are fundamental motifs in bioactive natural products and pharmaceuticals. Using simple toluene derivatives, a one-pot aminobenzylation of aldehydes is introduced that provides rapid access to amines. Simply combining benzaldehydes, toluenes, NaN(SiMe3)2, and additive Cs(O2CCF3) (0.35 equiv.) generates a diverse array of 1,2-diarylethylamine derivatives (36 examples, 56-98% yield). Furthermore, suitably functionalized 1,2-diarylethylamines were transformed into 2-aryl-substituted indoline derivatives via Buchwald-Hartwig amination. It is proposed that the successful deprotonation of toluene by MN(SiMe3)2 is facilitated by cation-π interactions between the arene and the group(I) cation that acidify the benzylic C-Hs.

| S-EPMC6105668 | biostudies-literature